N-(3-{(4S)-2-amino-4-[4-(difluoromethoxy)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}phenyl)-2-methoxyacetamide → N-(3-{(4R)-2-Amino-4-[4-(difluoromethoxy)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}phenyl)-2-methoxyacetamide

HRID 30560Notes

Reaction equation

HRID 30560 reaction equation
[NH2:1][C:2]1[N:3]([CH3:30])[C:4](=[O:29])[C@@:5]([C:17]2[CH:18]=[C:19]([NH:23][C:24](=[O:28])[CH2:25][O:26][CH3:27])[CH:20]=[CH:21][CH:22]=2)([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([F:16])[F:15])=[CH:9][CH:8]=2)[N:6]=1>CO>[NH2:1][C:2]1[N:3]([CH3:30])[C:4](=[O:29])[C@:5]([C:17]2[CH:18]=[C:19]([NH:23][C:24](=[O:28])[CH2:25][O:26][CH3:27])[CH:20]=[CH:21][CH:22]=2)([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH:14]([F:16])[F:15])=[CH:11][CH:12]=2)[N:6]=1

Participants

3

Reactant 1

HCID 16114151N-(3-{(4S)-2-amino-4-[4-(difluoromethoxy)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}phenyl)-2-methoxyacetamide

Product 1

HCID 16114066N-(3-{(4R)-2-Amino-4-[4-(difluoromethoxy)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}phenyl)-2-methoxyacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[B] N-(3-{(4S)-2-amino-4-[4-(difluoromethoxy)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}phenyl)-2-methoxyacetamide, MS m/e (M+H)+ 419; 1H NMR (400 MHz, DMSO-d6) 2.93 (s, 3H), 3.30 (s, 3H), 3.90 (s, 2H), 6.61 (brs, 2H), 7.08 (m, 3H), 7.2 (m, 2H), 7.44 (d, J=8.78 Hz, 2H), 7.55 (d, J=7.93 Hz, 1H), 7.62 (s, 1H), 9.71 (s, 1H); [a]25=−16 (C=1% in MeOH).

Sources & evidence

ORD record
ord-b2850d5bb70f43a1bd229f9cdbae5b45
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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