Ammonia → HCID 66558612, compound

HRID 331178Notes

Reaction equation

HRID 331178 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:4][C:3]=1[C@:22]1([CH3:34])[C:28]([F:30])([F:29])[C:27]([CH3:32])([CH3:31])[O:26][CH2:25][C:24](=S)[NH:23]1.[NH3:35]>C(OO)(C)(C)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[O:10][C:11]3[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:4][C:3]=1[C@:22]1([CH3:34])[C:28]([F:30])([F:29])[C:27]([CH3:32])([CH3:31])[O:26][CH2:25][C:24]([NH2:35])=[N:23]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86671897HCID 86671897, compound

Product 1

HCID 66558612HCID 66558612, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6410tert-Butyl hydroperoxideSolvent

Procedure

In a manner analogous to that described in Example 2c), the ammonolysis of (R)-5-[2,4-difluoro-5-(6-trifluoromethyl-benzooxazol-2-yl)-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-thione (110 mg, 217 μmol) with ammonia (7M in methanol; 2.14 ml) and tert-butylhydroperoxide (70% in water; 260 μl) yielded the title compound (33 mg, 31% yield). MS (ISP): m/z=490.2 [M+H]+.

Sources & evidence

ORD record
ord-28546b4227574ee5a51cca581eaea455
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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