Ethanol → 4-((1R,2S)-2-aminocyclohexylamino)-5-fluoro-2-(3-phenylisoxazol-5-ylamino)benzamide

HRID 2201093Notes

Reaction equation

HRID 2201093 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[C:16]([F:17])=[CH:15][C:12]([C:13]#[N:14])=[C:11]([NH:18][C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]=2)[CH:10]=1.CC[OH:32]>CS(C)=O.[OH-].[Na+].OO>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[C:16]([F:17])=[CH:15][C:12]([C:13]([NH2:14])=[O:32])=[C:11]([NH:18][C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]=2)[CH:10]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 677764004-((1R,2S)-2-aminocyclohexylamino)-5-fluoro-2-(3-phenylisoxazol-5-ylamino)benzonitrile

Product 1

HCID 692849184-((1R,2S)-2-aminocyclohexylamino)-5-fluoro-2-(3-phenylisoxazol-5-ylamino)benzamide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 784Hydrogen PeroxideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-((1R,2S)-2-aminocyclohexylamino)-5-fluoro-2-(3-phenylisoxazol-5-ylamino)benzonitrile in EtOH (1 mL) and DMSO (0.5 mL), 1N aq. NaOH (0.5 mL) and H2O2 (50% aq., 0.5 mL) were added. After being stirred at room temperature for 1 h, the mixture was concentrated in vacuo. The residue was acidified with HOAc (0.5 mL), and then was purified by HPLC to give the titled compound (33 mg). MS 410.3 (M+H); UV 204.7, 246.1, 287.8 nm.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customwas purified by HPLC

Sources & evidence

ORD record
ord-68cbd13c0e1c461d95f3c9e443036822
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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