Sulfuric Acid → HCID 178489040, compound

HRID 1595405Notes

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>>[CH2:3]([NH: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)[CH2:4][CH:5]([CH3:8])[CH3:6]

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 4311764Sodium borohydride

HCID 178489037HCID 178489037, compound

Product 1

HCID 178489040HCID 178489040, compoundYield 63.6%

Procedure

2-(4-Aminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (0.8 g) obtained in Example 48, sodium borohydride (0.13 g), 2.5N sulfuric acid (0.4 ml) and isopentyl aldehyde (0.3 ml) were treated in the same manner as in Example 72 to give 2-(4-isopentylaminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (0.3 g), melting point 235-239° C.

Sources & evidence

ORD record: ord-3948d3a24bf844ddb04ae417e7c9466d
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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