6-Chloro-3-Benzofuranone → (5R)-5-(5-(6-chloro-2,3-dihydrobenzofuran-3-ylamino)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione

HRID 403252Notes

Reaction equation

HRID 403252 reaction equation
[NH2:1][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](=[S:19])[NH:9]2)[CH:7]=1.[Cl:22][C:23]1[CH:32]=[CH:31][C:26]2[C:27](=O)[CH2:28][O:29][C:25]=2[CH:24]=1>>[Cl:22][C:23]1[CH:32]=[CH:31][C:26]2[CH:27]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]4([CH3:20])[C:14]([F:16])([F:15])[C:13]([CH3:17])([CH3:18])[O:12][CH2:11][C:10](=[S:19])[NH:9]4)[CH:7]=3)[CH2:28][O:29][C:25]=2[CH:24]=1

Participants

3

Reactant 2

HCID 137781336-Chloro-3-BenzofuranoneHCID 58563112(R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione

Product 1

HCID 86670908(5R)-5-(5-(6-chloro-2,3-dihydrobenzofuran-3-ylamino)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thioneYield 50.7%

Procedure

Prepared in an analogous manner as described for intermediate A22A from (R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione (intermediate A19B) (96 mg, 302 μmol) and commercially available 6-chlorobenzofuran-3(2H)-one [CAS no 3260-78-4] (61.0 mg, 362 μmol) The (5R)-5-(5-(6-chloro-2,3-dihydrobenzofuran-3-ylamino)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione (72 mg, 153 μmol, 50.7% yield) was obtained as a light yellow foam. MS (ISN): m/z=469.1 [(M−H)−] and 471.2 [(M+2-H)−].

Workup

  1. customPrepared in an analogous manner

Sources & evidence

ORD record
ord-9aa1e45e63d54861881dac7735150eab
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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