5-Amino-2-chloropyridine → (R)-5-(5-(6-chloropyridin-3-ylamino)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepan-3-one

HRID 403259Notes

Reaction equation

HRID 403259 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]2([CH3:20])[C:14]([F:16])([F:15])[C:13]([CH3:18])([CH3:17])[O:12][CH2:11][C:10](=[O:19])[NH:9]2)[CH:7]=1.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[N:27][CH:28]=1>>[Cl:29][C:26]1[N:27]=[CH:28][C:23]([NH:22][C:2]2[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]3([CH3:20])[C:14]([F:16])([F:15])[C:13]([CH3:18])([CH3:17])[O:12][CH2:11][C:10](=[O:19])[NH:9]3)[CH:7]=2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 793055-Amino-2-chloropyridineHCID 58562968(R)-5-(5-bromo-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepan-3-one

Product 1

HCID 86670911(R)-5-(5-(6-chloropyridin-3-ylamino)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepan-3-oneYield 32.7%

Procedure

Prepared in an analogous manner as described for intermediate A9A or A13A from (R)-5-(5-bromo-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepan-3-one (intermediate A16B) (200 mg, 546 μmol) and commercially available 5-amino-2-chloropyridine [CAS no 5350-93-6] (140 mg, 1.09 mmol). The (R)-5-(5-(6-chloropyridin-3-ylamino)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepan-3-one (74 mg, 32.7%) was obtained as a light brown foam. MS (ISP): m/z=414.2 [(M+H)+] and 416.2 [(M+2+H)+].

Workup

  1. customPrepared in an analogous manner

Sources & evidence

ORD record
ord-5bf950c94a9c4ef7b52f807eecbf6fd2
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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