Sulfuric Acid → HCID 178489036, compound

HRID 1595406Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:11]([C:13]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].S(=O)(=O)(O)O.[CH:36](=O)[CH2:37][CH2:38][CH2:39][CH:40]=O>>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:10]2[NH:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:1]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:3][CH:4]=3)=[N:12][C:11]=2[C:13]([NH:15][C:16]2[S:17][CH:18]=[CH:19][N:20]=2)=[O:14])=[CH:22][CH:23]=1

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 3485Glutaraldehyde

HCID 4311764Sodium borohydride

HCID 178489037HCID 178489037, compound

Product 1

HCID 178489036HCID 178489036, compound

Procedure

2-(4-Aminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (2.0 g) obtained in Example 48, sodium borohydride (0.8 g), 3N sulfuric acid (4 ml) and 25% glutaraldehyde (4 ml) were treated in the same manner as in Example 62 to give 5-(4-methoxyphenyl)-2-(4-piperidinophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (1.53 g). This was converted to hydrochloride to give 5-(4-methoxyphenyl)-2-(4-piperidinophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide hydrochloride (0.25 g), melting point 250° C. or above.

Sources & evidence

ORD record: ord-16caa577e4694129942ff731424629cc
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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