m-Chloroperbenzoic acid → HCID 68284428, compound

HRID 1527597Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:34])=[C:4]([C@H:8]([NH:10][C:11]([C@@H:13]2[CH2:18][C@@H:17]3[C@@H:15]([CH2:16]3)[N:14]2[C:19](=[O:33])[CH2:20][N:21]2[C:25]3=[CH:26][N:27]=[CH:28][CH:29]=[C:24]3[C:23]([C:30]([NH2:32])=[O:31])=[N:22]2)=[O:12])[CH3:9])[CH:5]=[CH:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:40]>C(O)(=O)C>[C:30]([C:23]1[C:24]2[C:25](=[CH:26][N+:27]([O-:40])=[CH:28][CH:29]=2)[N:21]([CH2:20][C:19]([N:14]2[C@H:13]([C:11](=[O:12])[NH:10][C@@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[F:34])[CH3:9])[CH2:18][C@@H:17]3[C@H:15]2[CH2:16]3)=[O:33])[N:22]=1)(=[O:31])[NH2:32]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 1-(2-((1R,3S,5R)-3-((R)-1-(3-chloro-2-fluorophenyl)ethylcarbamoyl)-2-azabicyclo[3.1.0]hexan-2-yl)-2-oxoethyl)-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (Example 702, 150 mg, 0.31 mmol) in acetic acid (4 mL) was added 3-chlorobenzoperoxoic acid (85 mg, 0.50 mmol) at 55° C. The reaction mixture was stirred at 55° C. for 18 h and then cooled to RT. Volatiles were evaporated and the residue was purified by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, flow: 40 mL/min, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA) to afford the title compound as a white solid. MS: 501 [M+H]+; tR (HPLC conditions c): 3.64 min.

Workup

temperaturecooled to RT
customVolatiles were evaporated
customthe residue was purified by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, flow: 40 mL/min, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA)

Sources & evidence

ORD record: ord-d7d78c21024d4f9c80b08e0f8a6d56c0
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085555B2

Reaction notes

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