5-(Propan-2-yl)-1,3-oxazole-4-carboxylic acid → 5-Isopropyl-oxazole-4-carboxylic acid [3-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide

HRID 1941850Notes

Reaction equation

HRID 1941850 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH3:17])[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]2)[CH:7]=1.[CH:19]([C:22]1[O:26][CH:25]=[N:24][C:23]=1[C:27](O)=[O:28])([CH3:21])[CH3:20]>>[NH2:16][C:10]1[O:11][CH2:12][C:13]([F:14])([F:15])[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:27]([C:23]3[N:24]=[CH:25][O:26][C:22]=3[CH:19]([CH3:21])[CH3:20])=[O:28])[CH:3]=[CH:4][C:5]=2[F:18])([CH3:17])[N:9]=1

Participants

3

Reactant 2

HCID 134887995-(Propan-2-yl)-1,3-oxazole-4-carboxylic acidHCID 58304207(R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

Product 1

HCID 532412045-Isopropyl-oxazole-4-carboxylic acid [3-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide

Procedure

The condensation of (R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate XI-1) and 5-isopropyl-oxazole-4-carboxylic acid following procedure I yielded the title compound as a white solid. MS (ISP): m/z=397.2 [M+H]+.

Sources & evidence

ORD record
ord-251421a0d8a94fe8ab18bfbb8be805d6
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

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