1-Methyl-3-aminopyrazole → (R)-N-(bis(4-methoxyphenyl)(phenyl)methyl)-6,6-difluoro-5-(2-fluoro-5-(1-methyl-1H-pyrazol-3-ylamino)phenyl)-5,7,7-trimethyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine

HRID 403231Notes

Reaction equation

HRID 403231 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[NH:10][C:11]2[CH2:12][O:13][C:14]([CH3:30])([CH3:29])[C:15]([F:28])([F:27])[C@:16]([C:19]3[CH:24]=[C:23](Br)[CH:22]=[CH:21][C:20]=3[F:26])([CH3:18])[N:17]=2)=[CH:5][CH:4]=1.[CH3:45][N:46]1[CH:50]=[CH:49][C:48]([NH2:51])=[N:47]1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[NH:10][C:11]2[CH2:12][O:13][C:14]([CH3:30])([CH3:29])[C:15]([F:28])([F:27])[C@:16]([C:19]3[CH:24]=[C:23]([NH:51][C:48]4[CH:49]=[CH:50][N:46]([CH3:45])[N:47]=4)[CH:22]=[CH:21][C:20]=3[F:26])([CH3:18])[N:17]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 68227452(R)-N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-bromo-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine

Product 1

HCID 68227365(R)-N-(bis(4-methoxyphenyl)(phenyl)methyl)-6,6-difluoro-5-(2-fluoro-5-(1-methyl-1H-pyrazol-3-ylamino)phenyl)-5,7,7-trimethyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amineYield 80.9%

Procedure

Prepared in an analogous manner as described for intermediate A9A or A13A from (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-bromo-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine (intermediate A8B) (210 mg, 315 μmol) and commercially available 1-methyl-1H-pyrazol-3-amine [CAS no 1904-31-0] (62.4 mg, 629 μmol). The (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-6,6-difluoro-5-(2-fluoro-5-(1-methyl-1H-pyrazol-3-ylamino)phenyl)-5,7,7-trimethyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine (174 mg, 80.9%) was obtained as a light yellow foam. MS (ISP): m/z=684 [M+H]+.

Workup

  1. customPrepared in an analogous manner

Sources & evidence

ORD record
ord-0017b94c7f94401fa1d35733d76699e1
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

Loading…