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

HRID 2408237노트

반응식

HRID 2408237 반응식
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]

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 132338443-(Trifluoromethyl)pyridine-2-carboxylic acidHCID 867072262-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzeneethanamine hydrochloride2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c2fd59c4b245462fb3335e083121635c
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815772B2

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