Triethylamine → 5-chloro-N-(3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 474344노트

반응식

HRID 474344 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[C:13]([NH2:14])=[CH:12][N:11]([CH3:15])[N:10]=1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:29]=[CH:28][N:27]2[N:30]=[CH:31][C:32]([C:33](Cl)=[O:34])=[C:26]2[N:25]=1>ClCCl>[Cl:23][C:24]1[CH:29]=[CH:28][N:27]2[N:30]=[CH:31][C:32]([C:33]([NH:14][C:13]3[C:9]([C:3]4[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=4[Cl:1])=[N:10][N:11]([CH3:15])[CH:12]=3)=[O:34])=[C:26]2[N:25]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 580630233-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-amineHCID 580631365-Chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride

생성물 1

HCID 580630965-chloro-N-(3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide수율 52.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To an ice-cooled solution of 3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-amine (121 mg, 0.50 mmol) and triethylamine (101 mg, 1.00 mmol) in dichloromethane (15 mL) was added 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (162 mg, 1.5 mmol). The reaction mixture was warmed to room temperature for 3 hours. The mixture was then washed with saturated aqueous sodium chloride solution. The collected organics were dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by preparative HPLC afforded 5-chloro-N-(3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide as a solid (110 mg, 52% yield). 1H NMR (400 MHz, DMSO-d6): 9.34 (d, J=7.6 Hz, 1H), 9.21 (s, 1H), 8.69 (s, 1H), 8.33 (s, 1H), 7.71 (d, J=9.2 Hz, 1H), 7.60 (d, J=9.2 Hz, 1H), 7.54 (s, 1H), 7.36 (d, J=6.8 Hz, 1H), 3.93 (s, 3H).

후처리

  1. washThe mixture was then washed with saturated aqueous sodium chloride solution
  2. dry with materialThe collected organics were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by preparative HPLC

출처 및 근거

ORD 기록
ord-ef4852d7f4724534a31a9dd1fca05b27
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637526B2

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