Ammonia → HCID 67462100, compound

HRID 1186190Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)=[O:10])=[CH:4][C:3]=1[C:18]12[CH2:25][CH:24]1[CH2:23][O:22][CH2:21][C:20](=S)[NH:19]2.[NH3:27].C(OO)(C)(C)C>CO>[NH2:27][C:20]1[CH2:21][O:22][CH2:23][CH:24]2[C:18]([C:3]3[CH:4]=[C:5]([NH:8][C:9]([C:11]4[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=4)=[O:10])[CH:6]=[CH:7][C:2]=3[F:1])([CH2:25]2)[N:19]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To mixture of 5-chloro-pyridine-2-carboxylic acid [4-fluoro-3-((1SR,7RS)-3-thioxo-5-oxa-2-aza-bicyclo[5.1.0]oct-1-yl)-phenyl]-amide (intermediate B14A) (142 mg, 0.36 mmol) and 7 N ammonia in methanol (3.1 ml) in methanol (15 ml) at 23° C. was added tert-butylhydroperoxide (70% in water, 0.50 ml, 3.62 mmol) and the mixture was stirred at 23° C. for 20 h. The reaction mixture was extracted with water and dichloromethane. The organic layer was washed with water and brine, the aqueous layers were reextracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a light yellow oil (180 mg, 132%), which was purified by silica gel column chromatography with dichloromethane to dichloromethane/methanol/ammonium hydroxide 65:10:1 to give the title compound as a white solid (10 mg, 7.4%). MS (ISP): m/z=375.3 [(M+H)+] and 377.3 [(M+2+H)+].

Workup

extractionThe reaction mixture was extracted with water and dichloromethane
washThe organic layer was washed with water and brine
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-2974d4c0e4de4e2fa582f4b9260b054a
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673894B2

Reaction notes

Loading…