Ammonia → HCID 66558866, compound

HRID 331172Notes

Reaction equation

HRID 331172 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:11]([F:30])=[CH:12][C:13]([F:29])=[C:14]([C@:16]4([CH3:28])[C:22]([F:24])([F:23])[C:21]([CH3:26])([CH3:25])[O:20][CH2:19][C:18](=S)[NH:17]4)[CH:15]=3)=[N:7][C:6]=2[CH:31]=1.[NH3:32].C(OO)(C)(C)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:11]([F:30])=[CH:12][C:13]([F:29])=[C:14]([C@:16]4([CH3:28])[C:22]([F:24])([F:23])[C:21]([CH3:26])([CH3:25])[O:20][CH2:19][C:18]([NH2:32])=[N:17]4)[CH:15]=3)=[N:7][C:6]=2[CH:31]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6410tert-Butyl hydroperoxideHCID 86671893HCID 86671893, compound

Product 1

HCID 66558866HCID 66558866, compoundYield 43%

Procedure

In a manner analogous to that described in Example 2c), the ammonolysis of (R)-5-[5-(5-chloro-benzo oxazol-2-yl)-2,4-difluoro-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-thione (35 mg, 74 μmol) with ammonia (7M in methanol; 0.73 ml) and tert-butylhydroperoxide (70% in water; 71 μl) yielded the title compound (14 mg, 43% yield). MS (ISP): m/z=456.3 [M+H]+ and 458.2 [M+2+H]+.

Sources & evidence

ORD record
ord-ee906c847faf437d8a4e6cdaab147437
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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