The present invention relates to a method for preparing primary amides from tertiary or secondary amides substituted with various alkyl groups through a transamidation reaction without a metal catalyst in room-temperature conditions by adding ammonium carbonate ((NH.sub.4).sub.2CO.sub.3), wherein the method is eco-friendly since various secondary and tertiary amides that are not toxic or corrosive are used as starting materials and ammonium carbonate ((NH.sub.4).sub.2CO.sub.3) that is neither a strong acid nor a strong base is used, and the method is economical since various primary amides can be synthesized with an excellent yield at room temperature without a metal catalyst.

The present invention relates to a method for preparing primary amides from tertiary or secondary amides substituted with various alkyl groups through a transamidation reaction without a metal catalyst in room-temperature conditions by adding ammonium carbonate ((NH.sub.4).sub.2CO.sub.3), wherein the method is eco-friendly since various secondary and tertiary amides that are not toxic or corrosive are used as starting materials and ammonium carbonate ((NH.sub.4).sub.2CO.sub.3) that is neither a strong acid nor a strong base is used, and the method is economical since various primary amides can be synthesized with an excellent yield at room temperature without a metal catalyst.

The present invention provided a process for manufacture of amantadine nitrate derivatives, and the process comprises using adamantane as the raw material to prepare amantadine nitrate derivatives via the following steps: (1) synthesis of adamantanol; (2) carboxylation of adamantanol; (3) acetylation of adamantanoic acid; (4) reduction; (5) hydrolysis of amido adamantanol and Boc protection of amino group; (6) crystallization of Boc protected amantadinol; (7) nitrate esterification of Boc protected amantadinol; (8) refining of the product of nitrate esterification; (9) Boc deprotection and salt formation; and (10) refining of amantadine nitrate hydrochloride. The amantadine nitrate derivatives have the struction of:

##STR00001##

wherein, R.sub.1 and R.sub.2 are each independently hydrogen, straight-chain or branched-chain alkyl, or substituted or unsubstituted aryl or heteroaryl. The process of this invention is efficient, cost effective, environmentally friendly, safe, reliable, and suitable for industrial production.

The present invention provided a process for manufacture of amantadine nitrate derivatives, and the process comprises using adamantane as the raw material to prepare amantadine nitrate derivatives via the following steps: (1) synthesis of adamantanol; (2) carboxylation of adamantanol; (3) acetylation of adamantanoic acid; (4) reduction; (5) hydrolysis of amido adamantanol and Boc protection of amino group; (6) crystallization of Boc protected amantadinol; (7) nitrate esterification of Boc protected amantadinol; (8) refining of the product of nitrate esterification; (9) Boc deprotection and salt formation; and (10) refining of amantadine nitrate hydrochloride. The amantadine nitrate derivatives have the struction of:

##STR00001##

wherein, R.sub.1 and R.sub.2 are each independently hydrogen, straight-chain or branched-chain alkyl, or substituted or unsubstituted aryl or heteroaryl. The process of this invention is efficient, cost effective, environmentally friendly, safe, reliable, and suitable for industrial production.

The invention relates to an improved process for synthesizing 6-(cyclopropaneamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl)amino)-N-(methyl-d3)pyridazine-3-carboxamide of the formula: ##STR00001## Compound I is currently in clinical trials for the treatment of auto-immune and auto-inflammatory diseases such as psoriasis.

The invention relates to an improved process for synthesizing 6-(cyclopropaneamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl)amino)-N-(methyl-d3)pyridazine-3-carboxamide of the formula: ##STR00001## Compound I is currently in clinical trials for the treatment of auto-immune and auto-inflammatory diseases such as psoriasis.

The present invention relates to new one-photon or two-photon absorbing fluorophores, a method for preparing the same, and a method for cellular imaging using the same, and more particularly, to new two-photon absorbing fluorophores having higher fluorescence quantum yield and two-photon absorption cross-section value than those of the conventional two-photon absorbing fluorophore, acedan, and thus are promisingly applicable in bioimaging. The design strategy and the compounds according to the present invention may practically utilized for developing new D-π-A fluorophores.

The present invention relates to new one-photon or two-photon absorbing fluorophores, a method for preparing the same, and a method for cellular imaging using the same, and more particularly, to new two-photon absorbing fluorophores having higher fluorescence quantum yield and two-photon absorption cross-section value than those of the conventional two-photon absorbing fluorophore, acedan, and thus are promisingly applicable in bioimaging. The design strategy and the compounds according to the present invention may practically utilized for developing new D-π-A fluorophores.

An object of this disclosure provides a novel method for producing a fluorovinyl amide compound and the like. The object is achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein
Rf is —F or fluoroalkyl,
R.sup.a1 is —H or an organic group, and
R.sup.a2 is —H or an organic group, or
(i) R.sup.a1 and R.sup.a2, (ii) R.sup.a1 and Rf, or (iii) Rf and R.sup.a2, may be linked to each other,
R.sup.b1 is —H or an organic group, and
R.sup.b2 is —H or an organic group, or
R.sup.b1 and R.sup.b2 may be linked together with their adjacent atoms to form a nitrogen-containing ring optionally having one or more substituents,
the method comprising
step A of reacting a compound represented by formula (2):

##STR00002##

wherein
R.sup.x is a leaving group,
with a compound represented by formula (3) or a salt thereof:

##STR00003##

in the presence of a transition metal catalyst.

An object of this disclosure provides a novel method for producing a fluorovinyl amide compound and the like. The object is achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein
Rf is —F or fluoroalkyl,
R.sup.a1 is —H or an organic group, and
R.sup.a2 is —H or an organic group, or
(i) R.sup.a1 and R.sup.a2, (ii) R.sup.a1 and Rf, or (iii) Rf and R.sup.a2, may be linked to each other,
R.sup.b1 is —H or an organic group, and
R.sup.b2 is —H or an organic group, or
R.sup.b1 and R.sup.b2 may be linked together with their adjacent atoms to form a nitrogen-containing ring optionally having one or more substituents,
the method comprising
step A of reacting a compound represented by formula (2):

##STR00002##

wherein
R.sup.x is a leaving group,
with a compound represented by formula (3) or a salt thereof:

##STR00003##

in the presence of a transition metal catalyst.