1-Hydroxybenzotriazole → N-[2-[2-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]ethyl]-3-(trifluoromethyl)-2-pyridinecarboxamide

HRID 2408237Notes

Reaction equation

HRID 2408237 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[N:10]2)[CH:6]=[CH:5][C:4]=1[CH2:18][CH2:19][NH2:20].ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[F:40][C:41]([F:52])([F:51])[C:42]1[C:43]([C:48](O)=[O:49])=[N:44][CH:45]=[CH:46][CH:47]=1>ClCCl>[Cl:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[N:10]2)[CH:6]=[CH:5][C:4]=1[CH2:18][CH2:19][NH:20][C:48]([C:43]1[C:42]([C:41]([F:52])([F:40])[F:51])=[CH:47][CH:46]=[CH:45][N:44]=1)=[O:49]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 132338443-(Trifluoromethyl)pyridine-2-carboxylic acidHCID 867072262-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzeneethanamine hydrochloride2×

Product 1

HCID 86707228N-[2-[2-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]ethyl]-3-(trifluoromethyl)-2-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzeneethanamine hydrochloride (1:1) (i.e. the product of Step C; 300 mg, 1.11 mmol), N-(3-dimethyl-aminopropyl)-N′-ethylcarbodiimide (297 mg, 1.66 mmol), 1-hydroxybenzotriazole (212 mg, 1.66 mmol) and N,N-diisopropylethylamine (0.9 mL, 5.55 mmol) in dichloromethane (15 mL) was added 3-(trifluoromethyl)pyridine-2-carboxylic acid (198 mg, 1.21 mmol), and the resulting mixture was stirred for 12 h. The reaction mixture was washed with water and brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with 50% ethyl acetate in hexanes to afford the title compound (210 mg) as a brown solid.

Workup

  1. washThe reaction mixture was washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluted with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c2fd59c4b245462fb3335e083121635c
Source dataset
uspto-grants-2014_08
Patent number
US08815772B2

Reaction notes

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