Benzenepropanoyl chloride → HCID 11488539, compound

HRID 1689846Notes

Reaction equation

HRID 1689846 reaction equation
[C:1](Cl)(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:36])([F:35])[F:34])=[O:26])[CH2:21][CH2:20]2)=[N:17][CH:18]=1>ClCCl.C(N(C(C)C)CC)(C)C>[C:4]1([CH2:3][CH2:2][C:1]([NH:12][C:13]2[CH:18]=[N:17][C:16]([N:19]3[CH2:20][CH2:21][N:22]([C:25](=[O:26])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:36])([F:35])[F:34])[CH2:23][CH2:24]3)=[CH:15][CH:14]=2)=[O:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 66905728HCID 66905728, compound

Product 1

HCID 11488539HCID 11488539, compoundYield 7.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
25 °C

Procedure

Hydrocinnamoyl chloride (0.037 mL, 0.25 mmol) in dichloromethane was added to a solution of [4-(5-aminopyridin-2-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone (0.070 g, 0.20 mmol) in dichloromethane (2 mL) and diisopropylethylamine (0.087 mL) at 0° C. The mixture was stirred at 25° C. for 16 h and then diluted with dichloromethane. The organic phase was washed with water and saturated NaCl solution, dried over anhydrous MgSO4. After removal of dichloromethane, the title compound was obtained in 7.6% yield (7.3 mg) after column purification. 1H NMR (300 MHz, CDCl3) δ 7.99, 7.80, 7.71, 7.56, 7.27, 6.91, 6.61, 3.91, 3.57, 3.43, 3.27, 3.04, 2.64. MS (ES+) m/z 483.0 (M+1).

Workup

  1. washThe organic phase was washed with water and saturated NaCl solution
  2. dry with materialdried over anhydrous MgSO4
  3. customAfter removal of dichloromethane

Sources & evidence

ORD record
ord-272a7cf8cdd845ab8c2c492c442a841e
Source dataset
uspto-grants-2012_04
Patent number
US08153636B2

Reaction notes

Loading…