2,2-dimethyl-N-[2-methyl-2-(4-nitro-1H-imidazol-1-yl)propyl]propan-1-amine → (S)-2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-N-{1-[2-(2,2-dimethyl-propylamino)-1,1-dimethyl-ethyl]-1H-imidazol-4-yl}-2-phenyl-acetamide

HRID 505057Notes

Reaction equation

HRID 505057 reaction equation
[CH3:1][C:2]([N:11]1[CH:15]=[C:14]([N+:16]([O-])=O)[N:13]=[CH:12]1)([CH3:10])[CH2:3][NH:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7].[F:19][C:20]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]2[C:21]=1[CH2:22][CH:23]([NH:31][C@@H:32]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:33](O)=[O:34])[CH2:24][CH2:25]2>>[F:30][C:28]1[CH:27]=[C:26]2[C:21](=[C:20]([F:19])[CH:29]=1)[CH2:22][CH:23]([NH:31][C@@H:32]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:33]([NH:16][C:14]1[N:13]=[CH:12][N:11]([C:2]([CH3:10])([CH3:1])[CH2:3][NH:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH:15]=1)=[O:34])[CH2:24][CH2:25]2

Participants

3

Reactant 2

HCID 671640862,2-dimethyl-N-[2-methyl-2-(4-nitro-1H-imidazol-1-yl)propyl]propan-1-amineHCID 68464622(S)-2-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-3-ylamino)-2-phenylacetic acid

Product 1

HCID 16113686(S)-2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-N-{1-[2-(2,2-dimethyl-propylamino)-1,1-dimethyl-ethyl]-1H-imidazol-4-yl}-2-phenyl-acetamide

Procedure

2-methyl-N-neopentyl-2-(4-nitro-1H-imidazol-1-yl)propan-1-amine (U.S. Ser. No. 11/078,898 filed Mar. 11, 2005) was reduced and coupled with (S)-2-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-3-ylamino)-2-phenylacetic acid to afford the title compound: MS 524 m/z (M+1).

Sources & evidence

ORD record
ord-a81460a5a433475da25d8435bd1daba2
Source dataset
uspto-grants-2010_08
Patent number
US07781435B2

Reaction notes

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