tert-butyl (1S,2R)-2-(4-carbamoyl-3-(3-phenylisoxazol-5-ylamino)phenylamino)cyclohexylcarbamate → 4-((1R,2S)-2-aminocyclohexylamino)-2-(3-phenylisoxazol-5-ylamino)benzamide

HRID 2201031Notes

Reaction equation

HRID 2201031 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17]C(=O)OC(C)(C)C)=[CH:6][C:5]=1[NH:25][C:26]1[O:30][N:29]=[C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=1)(=[O:3])[NH2:2]>C(O)(C(F)(F)F)=O>[NH2:17][C@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:1]([NH2:2])=[O:3])=[C:5]([NH:25][C:26]2[O:30][N:29]=[C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:27]=2)[CH:6]=1

Participants

3

Reactant 1

HCID 69284828tert-butyl (1S,2R)-2-(4-carbamoyl-3-(3-phenylisoxazol-5-ylamino)phenylamino)cyclohexylcarbamate

Product 1

HCID 573341844-((1R,2S)-2-aminocyclohexylamino)-2-(3-phenylisoxazol-5-ylamino)benzamideYield 20.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound tert-butyl (1S,2R)-2-(4-carbamoyl-3-(3-phenylisoxazol-5-ylamino)phenylamino)cyclohexylcarbamate (6 mg) was dissolved in TFA (1 mL). After 10 min of standing, TFA removed in vacuo. The residue was purified by HPLC to give the titled compound (1 mg). MS 392.4 (M+H); UV 202.9, 294.0 nm

Workup

  1. customAfter 10 min of standing, TFA removed in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-bb99c6388cc54999a3122392c8d5cf3e
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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