N-Trimethylsilyl-N-methylacetamide → 1-Isopropylsulfonyl-2-amino-6-(alpha-hydroxy-alpha-methylaminocarbonylmethylbenzyl)benzimidazole

HRID 904829Notes

Reaction equation

[CH3:1][N:2]([Si](C)(C)C)[C:3](=[O:5])[CH3:4].[CH:10]([S:13]([N:16]1[C:20]2[CH:21]=[C:22]([C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[NH2:33])(=[O:15])=[O:14])([CH3:12])[CH3:11].C([Li])CCC>>[CH:10]([S:13]([N:16]1[C:20]2[CH:21]=[C:22]([C:25]([OH:32])([CH2:4][C:3]([NH:2][CH3:1])=[O:5])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[NH2:33])(=[O:14])=[O:15])([CH3:12])[CH3:11]

Participants

Reactant 3

HCID 81953N-Trimethylsilyl-N-methylacetamide

HCID 30173892-Amino-6-benzoyl-1-((isopropyl)sulphonyl)-1H-benzimidazole

HCID 178418339Butyllithium

Product 1

HCID 132864991-Isopropylsulfonyl-2-amino-6-(alpha-hydroxy-alpha-methylaminocarbonylmethylbenzyl)benzimidazole

Procedure

Following the general procedure of Example 23, N-methyl-N-trimethylsilylacetamide was reacted with 1-isopropylsulfonyl-2-amino-6-benzoylbenzimidazole in the presence of n-butyl lithium to provide 1-isopropylsulfonyl-2-amino-6-(α-hydroxy-α-methylaminocarbonylmethylbenzyl)benzimidazole. M.P. 92°-95° C.

Sources & evidence

ORD record: ord-f4e5e231920543f78ea358305d2adef3
Source dataset: uspto-grants-1983_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04420479

Reaction notes

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