4-Fluoroaniline → HCID 68227496, compound

HRID 403258Notes

Reaction equation

HRID 403258 reaction equation
[F:1][C:2]1([F:13])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=[O:11])[NH:4][CH:3]1[CH3:12].[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>>[F:13][C:2]1([F:1])[C:8]([CH3:9])([CH3:10])[O:7][CH2:6][C:5](=[O:11])[NH:4][C@@:3]1([C:16]1[CH:17]=[C:18]([NH:19][C:18]2[CH:20]=[CH:21][C:15]([F:14])=[CH:16][CH:17]=2)[CH:20]=[CH:21][C:15]=1[F:14])[CH3:12]

Participants

3

Reactant 2

HCID 97314-Fluoroaniline2×HCID 86670910HCID 86670910, compound

Product 1

HCID 68227496HCID 68227496, compoundYield 55.7%

Procedure

Prepared in an analogous manner as described for intermediate A9A or A13A from (R)-545-bromo-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepan-3-one (intermediate A16B) (300 mg, 819 μmol) and commercially available 4-fluoroaniline [CAS no 371-40-4] 4-fluoroaniline (157 μL, 1.64 mmol). The (R)-6,6-difluoro-5-(2-fluoro-5-(4-fluorophenylamino)phenyl)-5,7,7-trimethyl-1,4-oxazepan-3-one (181 mg, 55.7%) was obtained as a light yellow foam. MS (ISP): m/z=397.0 [(M+H)+].

Workup

  1. customPrepared in an analogous manner

Sources & evidence

ORD record
ord-fa433a5bff124583aae64613c91a9b68
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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