2-(Dimethyl-1,2-oxazol-4-yl)acetic acid → HCID 25255569, compound

HRID 507423Notes

Reaction equation

HRID 507423 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:27])[CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]2[CH3:26])=[C:4]([F:28])[CH:3]=1.[CH3:29][C:30]1[C:34]([CH2:35][C:36](O)=[O:37])=[C:33]([CH3:39])[O:32][N:31]=1>>[CH3:29][C:30]1[C:34]([CH2:35][C:36]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:27])[CH2:9][N:10]3[C:14](=[O:15])[C:13]([C:19]4[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=4)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]3[CH3:26])=[C:4]([F:28])[CH:3]=2)=[O:37])=[C:33]([CH3:39])[O:32][N:31]=1

Participants

3

Reactant 2

HCID 20633382-(Dimethyl-1,2-oxazol-4-yl)acetic acidHCID 684625703-[2-(4-Amino-2-fluoro-phenyl)-2-oxo-ethyl]-5-(4-fluoro-phenyl)-2-methyl-5-propyl-3,5-dihydro-imidazol-4-one

Product 1

HCID 25255569HCID 25255569, compound

Procedure

Synthesis in analogy to Example 14 and Example 1 starting from enantiomerically pure 3-[2-(4-amino-2-fluoro-phenyl)-2-oxo-ethyl]-5-(4-fluoro-phenyl)-2-methyl-5-propyl-3,5-dihydro-imidazol-4-one and (3,5-dimethylisoxazol-4-yl)-acetic acid to yield (−)-2-(3,5-dimethyl-isoxazol-4-yl)-N-(3-fluoro-4-{2-[4-(4-fluoro-phenyl)-2-methyl-5-oxo-4-propyl-4,5-dihydro-imidazol-1-yl]-acetyl}-phenyl)-acetamide. LC/MS at 254 nm; [M+H] 523; Rt 3.417 min; optical rotation αD25−1.4°, c=0.5 in methanol.

Sources & evidence

ORD record
ord-a24f085e0ac7480d9513687fdbada516
Source dataset
uspto-grants-2010_08
Patent number
US07786155B2

Reaction notes

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