Butanal → HCID 178448792, compound

HRID 1595404Notes

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][CH3:39]>>[CH2:36]([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)[CH2:37][CH2:38][CH3:39]

Participants

Reactant 4

HCID 261Butanal

HCID 1118Sulfuric Acid

HCID 4311764Sodium borohydride

HCID 178489037HCID 178489037, compound

Product 1

HCID 178448792HCID 178448792, compound

Procedure

2-(4-Aminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (1.0 g) obtained in Example 48, sodium borohydride (0.13 g), 4N sulfuric acid (0.2 ml) and butyraldehyde (0.3 ml) were treated in the same manner as in Example 72 to give 2-(4-butylaminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (1.1 g). This was converted to hydrochloride to give 2-(4-butylaminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide hydrochloride (0.20 g), melting point 250° C. or above.

Sources & evidence

ORD record: ord-a68910ad468f4ad1aac602701c18cc27
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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