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

HRID 1927593Notes

Reaction equation

HRID 1927593 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])[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]([CH:14]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:16])[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 693036392-[1-(4-amino-2-fluoro-phenyl)-piperidin-4-yl]-N,N-diethyl-2-phenyl-acetamide

Product 1

HCID 166670902-(1-{4-[3-(3,5-Dimethyl-isoxazol-4-yl)-ureido]-2-fluoro-phenyl}-piperidin-4-yl)-N,N-diethyl-2-phenyl-acetamideYield 50%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-[1-(4-amino-2-fluoro-phenyl)-piperidin-4-yl]-N,N-diethyl-2-phenyl-acetamide (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 precipitate that had formed was collected by filtration and dried under vacuum to give the title compound (78 mg, 50%). MS (ESI): mass calcd. for C29H36FN5O3, 521.28; m/z found, 522.4 [M+H]+. 1H NMR (CDCl3): 7.95-7.75 (br s, 1H), 7.40-7.20 (m, 5H), 7.30-6.90 (br s, 1H), 6.80-6.70 (m, 2H), 3.60-3.10 (m, 7H), 2.45-2.35 (m, 2H), 2.28 (s, 3H), 2.20-2.10 (m, 4H), 2.00-1.90 (m, 1H), 1.52-1.40 (m, 1H), 1.35-1.20 (m, 2H), 1.18-1.03 (m, 6H).

Workup

  1. customThe precipitate that had formed
  2. filtrationwas collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a1ae2e4675454e7db9ec1931b402c7b7
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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