m-Chloroperbenzoic acid → HCID 71009666, compound

HRID 1527596Notes

Reaction equation

HRID 1527596 reaction equation
[Cl:1][C:2]1[C:3]([F:33])=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][NH:6][C:7]([C@@H:9]1[CH2:14][C@@H:13]2[C@@H:11]([CH2:12]2)[N:10]1[C:15](=[O:29])[CH2:16][N:17]1[C:21]2=[CH:22][N:23]=[CH:24][CH:25]=[C:20]2[C:19]([C:26]([NH2:28])=[O:27])=[N:18]1)=[O:8].ClC1C=C(C=CC=1)C(OO)=[O:39]>C(O)(=O)C>[C:26]([C:19]1[C:20]2[C:21](=[CH:22][N+:23]([O-:39])=[CH:24][CH:25]=2)[N:17]([CH2:16][C:15]([N:10]2[C@H:9]([C:7](=[O:8])[NH:6][CH2:5][C:4]3[CH:30]=[CH:31][CH:32]=[C:2]([Cl:1])[C:3]=3[F:33])[CH2:14][C@@H:13]3[C@H:11]2[CH2:12]3)=[O:29])[N:18]=1)(=[O:27])[NH2:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68283861HCID 68283861, compound

Product 1

HCID 71009666HCID 71009666, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 1-(2-((1R,3S,5R)-3-(3-chloro-2-fluorobenzylcarbamoyl)-2-azabicyclo[3.1.0]hexan-2-yl)-2-oxoethyl)-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (Example 703, 100 mg, 0.21 mmol) in acetic acid (4 mL) was added 3-chlorobenzoperoxoic acid (58 mg, 0.34 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: 487 [M+H]+; tR (HPLC conditions c): 3.44 min.

Workup

  1. temperaturecooled to RT
  2. customVolatiles were evaporated
  3. 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-10681a7d3b944a67ba10d1d47d3d07b3
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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