Potassium Carbonate → N-[4-Carbamoylmethoxy-3-(4-chloro-2-methyl-2H-pyrazol-3-yl)-phenyl]-3-trifluoromethyl-benzamide

HRID 521628Notes

Reaction equation

HRID 521628 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:27])[C:6]=1[C:7]1[CH:8]=[C:9]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH:10]=[CH:11][C:12]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]([NH2:38])=[O:37]>CC(C)=O>[C:36]([CH2:35][O:13][C:12]1[CH:11]=[CH:10][C:9]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)=[CH:8][C:7]=1[C:6]1[N:5]([CH3:27])[N:4]=[CH:3][C:2]=1[Cl:1])(=[O:37])[NH2:38]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 136387987HCID 136387987, compound

Product 1

HCID 57814678N-[4-Carbamoylmethoxy-3-(4-chloro-2-methyl-2H-pyrazol-3-yl)-phenyl]-3-trifluoromethyl-benzamideYield 83.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of N-(3-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-hydroxyphenyl)-3-(trifluoromethyl)benzamide (51 mg, 0.13 mmol) and potassium carbonate (27 mg, 0.20 mmol) in acetone (1 mL) was added 2-bromoacetamide (27 mg, 0.20 mmol). The resultant mixture was heated to 65° C. for 1 hour. Cooled to room temperature and partitioned between EtOAc and water. Layers were separated. The organic layer was washed with water (2×) and brine, dried (MgSO4) and reduced to give the title compound as a white solid (49 mg, 83%). LCMS m/z (%)=453 (M+H 35Cl, 100), 455 (M+H 37Cl, 30). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.73 (s, 3H), 4.46-4.61 (m, 2H), 7.09 (d, J=9.09 Hz, 1H), 7.24 (s, 1H), 7.38 (s, 1H), 7.65 (s, 1H), 7.72 (d, J=2.78 Hz, 1H), 7.73-7.84 (m, 1H), 7.87 (dd, J=8.97, 2.65 Hz, 1H), 7.97 (d, J=6.57 Hz, 1H), 8.21-8.36 (m, 2H), 10.53 (s, 1H).

Workup

  1. custompartitioned between EtOAc and water
  2. customLayers were separated
  3. washThe organic layer was washed with water (2×) and brine
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-38242101092148c49195138a43eb7b0b
Source dataset
uspto-grants-2016_05
Patent number
US09328107B2

Reaction notes

Loading…