HCID 57497168, compound → (R)-5-{5-[(4-Chloro-1-difluoromethyl-1H-pyrazol-3-ylmethyl)-amino]-2-fluoro-phenyl}-5-ethyl-6,6-difluoro-2,5,6,7-tetrahydro-[1,4]oxazepin-3-ylamine

HRID 403272Notes

Reaction equation

HRID 403272 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@:8]2([CH2:18][CH3:19])[C:14]([F:16])([F:15])[CH2:13][O:12][CH2:11][C:10]([NH2:17])=[N:9]2)[CH:7]=1.[Cl:21][C:22]1[C:23]([CH:30]=O)=[N:24][N:25]([CH:27]([F:29])[F:28])[CH:26]=1>>[Cl:21][C:22]1[C:23]([CH2:30][NH:1][C:2]2[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@:8]3([CH2:18][CH3:19])[C:14]([F:15])([F:16])[CH2:13][O:12][CH2:11][C:10]([NH2:17])=[N:9]3)[CH:7]=2)=[N:24][N:25]([CH:27]([F:29])[F:28])[CH:26]=1

Participants

3

Reactant 2

HCID 57497168HCID 57497168, compoundHCID 58563050(R)-5-(5-amino-2-fluoro-phenyl)-5-ethyl-6,6-difluoro-2,5,6,7-tetrahydro-[1,4]oxazepin-3-ylamine

Product 1

HCID 66547318(R)-5-{5-[(4-Chloro-1-difluoromethyl-1H-pyrazol-3-ylmethyl)-amino]-2-fluoro-phenyl}-5-ethyl-6,6-difluoro-2,5,6,7-tetrahydro-[1,4]oxazepin-3-ylamineYield 23.2%

Procedure

In an analogous manner as described for example 2 the reductive amination of (R)-5-(5-amino-2-fluoro-phenyl)-5-ethyl-6,6-difluoro-2,5,6,7-tetrahydro-[1,4]oxazepin-3-ylamine (intermediate A10F) (28.7 mg, 100 μmol) and 4-chloro-1-difluoromethyl-1H-pyrazole-3-carbaldehyde (19.9 mg, 110 μmol) yielded the title compound (10.5 mg, 23.2%) as a colorless oil. MS (ISP): m/z=452.1 [M+H]+and 454.1 [(M+2+H)+].

Sources & evidence

ORD record
ord-b2a7404435ad41a39e9cfdcfe056bc38
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

Loading…