3,5-Dimethylisoxazole-4-isocyanate → N-(1-{4-[3-(3,5-Dimethyl-isoxazol-4-yl)-ureido]-2-fluoro-phenyl}-piperidin-4-yl)-2-ethyl-N-phenyl-butyramide

HRID 1927601Notes

Reaction equation

HRID 1927601 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15](=[O:21])[CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH2:10][CH2:9]2)=[C:4]([F:28])[CH:3]=1.[N:29]([C:32]1[C:33]([CH3:38])=[N:34][O:35][C:36]=1[CH3:37])=[C:30]=[O:31]>ClCCCl>[CH3:38][C:33]1[C:32]([NH:29][C:30](=[O:31])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][CH:11]([N:14]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:15](=[O:21])[CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH2:10][CH2:9]3)=[C:4]([F:28])[CH:3]=2)=[C:36]([CH3:37])[O:35][N:34]=1

Participants

4

Reactant 2

HCID 27362663,5-Dimethylisoxazole-4-isocyanateHCID 69305096N-[1-(4-amino-2-fluoro-phenyl)-piperidin-4-yl]-2-ethyl-N-phenyl-butyramide

Product 1

HCID 16667231N-(1-{4-[3-(3,5-Dimethyl-isoxazol-4-yl)-ureido]-2-fluoro-phenyl}-piperidin-4-yl)-2-ethyl-N-phenyl-butyramideYield 36%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of N-[1-(4-amino-2-fluoro-phenyl)-piperidin-4-yl]-2-ethyl-N-phenyl-butyramide (0.30 mmol) and 4-isocyanato-3,5-dimethyl-isoxazole (1.0 mmol) in DCE (10 mL) was stirred at rt for 16 h. The mixture was concentrated and the residue was purified by PTLC to give the title compound (56 mg, 36%). MS (ESI): mass calcd. for C29H36FN5O3, 521.28. m/z found, 522.4 [M+H]+. 1H NMR (CDCl3): 8.00-7.82 (br s, NH), 7.55-7.41 (m, 4H), 7.20-7.11 (m, 2H), 7.10-6.95 (br s, NH), 6.94-6.75 (m, 2H), 4.90-4.72 (m, 1H), 3.40-3.22 (m, 2H), 2.66-2.57 (m, 2H), 2.33 (s, 3H), 2.24 (s, 3H), 2.09-2.00 (m, 1H), 1.94-1.85 (m, 2H).1.70-1.58 (m, 2H), 1.57-1.45 (m, 2H), 1.42-1.30 (m, 2H), 0.85 (t, J=7.2, 6H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by PTLC

Sources & evidence

ORD record
ord-1e5ad55c2cb24dcd8b5b9e095c4578d7
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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