5-(2,2-Difluoroethoxy)pyrazine-2-carboxylic acid → N-(3-((4S,6S)-2-Amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-(2,2-difluoroethoxyl)pyrazine-2-carboxamide

HRID 2178163Notes

Reaction equation

HRID 2178163 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]2([CH2:19][F:20])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH2:18])=[N:9]2)[CH:7]=1.[F:22][CH:23]([F:35])[CH2:24][O:25][C:26]1[N:27]=[CH:28][C:29]([C:32](O)=[O:33])=[N:30][CH:31]=1>>[NH2:18][C:10]1[O:11][C@H:12]([C:14]([F:17])([F:15])[F:16])[CH2:13][C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:32]([C:29]3[CH:28]=[N:27][C:26]([O:25][CH2:24][CH:23]([F:35])[F:22])=[CH:31][N:30]=3)=[O:33])[CH:3]=[CH:4][C:5]=2[F:21])([CH2:19][F:20])[N:9]=1

Participants

3

Reactant 2

HCID 578274665-(2,2-Difluoroethoxy)pyrazine-2-carboxylic acidHCID 86732112(4S,6S)-4-(5-amino-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Product 1

HCID 71665989N-(3-((4S,6S)-2-Amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-(2,2-difluoroethoxyl)pyrazine-2-carboxamide

Procedure

The coupling of (4S,6S)-4-(5-amino-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (XI-2) and 5-(2,2-difluoroethoxyl)pyrazine-2-carboxylic acid [Y. Suzuki et al. WO2009091016 (2009)] following General Procedure G yielded the title compound as a colorless solid. MS: m/z=496.6 [M+H]+.

Sources & evidence

ORD record
ord-85b370168a10420a9d4443b3a78063fe
Source dataset
uspto-grants-2015_06
Patent number
US09067926B2

Reaction notes

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