3-Chloro-5-cyanopyridine-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)-3-chloro-5-cyanopicolinamide formate

HRID 1186196Notes

Reaction equation

HRID 1186196 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.[Cl:20][C:21]1[C:22]([C:29]([OH:31])=[O:30])=[N:23][CH:24]=[C:25]([C:27]#[N:28])[CH:26]=1>>[CH:29]([OH:31])=[O:30].[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:29](=[O:30])[C:22]3[C:21]([Cl:20])=[CH:26][C:25]([C:27]#[N:28])=[CH:24][N:23]=3)[CH:3]=[CH:4][C:5]=2[F:19])([CH3:18])[N:9]=1

Participants

3

Reactant 2

HCID 508531763-Chloro-5-cyanopyridine-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 54577577(R)-N-(3-(3-amino-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-5-yl)-4-fluorophenyl)-3-chloro-5-cyanopicolinamide 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 3-chloro-5-cyano-pyridine-2-carboxylic acid (prepared according to Hori, A. et al., Int. Patent Application Publ. No. WO2009151098) yielded the title compound as a pale yellow solid. MS (ISP): m/z=438.1 [M+H]+.

Sources & evidence

ORD record
ord-d65bbcf98163483e94a9f2822a579274
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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