5-(2,2-Difluoroethoxy)pyrazine-2-carboxylic acid → (R)-N-(3-(3-Amino-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-5-yl)-4-fluorophenyl)-5-(2,2-difluoroethoxy)pyrazine-2-carboxamide formate

HRID 1186204Notes

Reaction equation

HRID 1186204 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C@:8]2([CH3:18])[C:14]([F:16])([F:15])[CH2:13][O:12][CH2:11][C:10]([NH2:17])=[N:9]2)[CH:7]=1.[F:20][CH:21]([F:33])[CH2:22][O:23][C:24]1[N:25]=[CH:26][C:27]([C:30]([OH:32])=[O:31])=[N:28][CH:29]=1>>[CH:30]([OH:32])=[O:31].[NH2:17][C:10]1[CH2:11][O:12][CH2:13][C:14]([F:15])([F:16])[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:30]([C:27]3[CH:26]=[N:25][C:24]([O:23][CH2:22][CH:21]([F:33])[F:20])=[CH:29][N:28]=3)=[O:31])[CH:3]=[CH:4][C:5]=2[F:19])([CH3:18])[N:9]=1

Participants

3

Reactant 2

HCID 578274665-(2,2-Difluoroethoxy)pyrazine-2-carboxylic acidHCID 58562966(R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine

Product 1

HCID 54578226(R)-N-(3-(3-Amino-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-5-yl)-4-fluorophenyl)-5-(2,2-difluoroethoxy)pyrazine-2-carboxamide formate

Procedure

The coupling of (R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine (intermediate A10A) and 5-(2,2-difluoro-ethoxy) -pyrazine-2-carboxylic acid (prepared according to Suzuki, Y. et al., Int. Patent Application Publ. No. WO2009091016) yielded the title compound as a light yellow solid. MS (ISP): m/z=460.1 [M+H]+.

Sources & evidence

ORD record
ord-1311066e7a834c3a9944d4c88285bc9e
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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