2-(Trifluoromethyl)benzoyl chloride → HCID 11432324, compound

HRID 1661879Notes

Reaction equation

HRID 1661879 reaction equation
[CH3:1][CH:2]([CH3:24])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:9]([C:20]([F:23])([F:22])[F:21])=[N:10][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[N:12][CH:13]=1)=[O:7].C(N(C(C)C)CC)(C)C.[F:34][C:35]([F:46])([F:45])[C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38](Cl)=[O:39]>ClCCl>[CH3:1][CH:2]([CH3:24])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:9]([C:20]([F:23])([F:21])[F:22])=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:38](=[O:39])[C:37]3[CH:41]=[CH:42][CH:43]=[CH:44][C:36]=3[C:35]([F:34])([F:45])[F:46])[CH2:16][CH2:15]2)=[N:12][CH:13]=1)=[O:7]

Participants

5

Reactant 3

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 67174367HCID 67174367, compound

Product 1

HCID 11432324HCID 11432324, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of 2-piperazin-1-yl-4-trifluoromethyl-pyrimidine-5-carboxylic acid (3-methylbutyl)amide (0.323 g, 0.935 mmol) in dichloromethane (20 mL) was added diisopropylethylamine (0.242 mL, 1.40 mmol). The mixture was stirred for 10 minutes before 2-trifluoromethylbenzoyl chloride (0.175 g, 0.842 mmol) in 5 mL dichloromethane was added. The stirring was continued for another 15 minutes. The reaction was quenched by the addition of saturated sodium bicarbonate solution, followed by water. The mixture was extracted with dichloromethane, and the organic layer was separated, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound in yield 76% (0.225 g, 0.435 mmol). 1H NMR (CDCl3) δ 8.59, 7.73-7.71, 7.64-7.51, 7.35-7.33, 5.76, 4.09-3.74, 3.44-3.37, 3.26-3.22, 1.68-1.59, 1.48-1.41, 0.09. MS (ES+) m/z 518.2 (M+1).

Workup

  1. additionwas added
  2. customThe reaction was quenched by the addition of saturated sodium bicarbonate solution
  3. extractionThe mixture was extracted with dichloromethane
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fdb2be87cd47408794251aceef67f181
Source dataset
uspto-grants-2011_10
Patent number
US08030488B2

Reaction notes

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