Diisopropylethylamine → 5-chloro-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 474323노트

반응식

HRID 474323 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11](Cl)=[O:12])=[C:4]2[N:3]=1.[Cl:14][C:15]1[CH:16]=[C:17]([N:21]2[C:25]([NH2:26])=[CH:24][C:23]([CH3:27])=[N:22]2)[CH:18]=[CH:19][CH:20]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:26][C:25]3[N:21]([C:17]4[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[CH:16]=4)[N:22]=[C:23]([CH3:27])[CH:24]=3)=[O:12])=[C:4]2[N:3]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 18106301-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amineHCID 580631365-Chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride

생성물 1

HCID 580633975-chloro-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide수율 95.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (150 mg, 0.69 mM, 1.0 equiv), 1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amine (140 mg, 0.69 mM, 1.0 equiv, available from Enamine, Ltd, Cincinnati, Ohio Cat# EN300-02447), N,N-diisopropylethylamine (0.18 mL, 1.0 mM, 1.0 equiv), and 15 mL of dichloromethane was stirred at ambient temperature for 3 days. The reaction was partitioned between dichloromethane and water. The dichloromethane phase was dried over sodium sulfate and vacuum filtered through silica gel. The silica gel pad was washed with 95:5 dichloromethane:methanol. The combined filtrates were concentrated to give 250 mg (93%) of 5-chloro-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide which was 74% pure by HPLC and used without further purification. LCMS (ESI) m+H=387.2, (two chlorine isotope pattern).

후처리

  1. customThe reaction was partitioned between dichloromethane and water
  2. dry with materialThe dichloromethane phase was dried over sodium sulfate and vacuum
  3. filtrationfiltered through silica gel
  4. washThe silica gel pad was washed with 95:5 dichloromethane
  5. concentrationThe combined filtrates were concentrated

출처 및 근거

ORD 기록
ord-41207d98790c41d3a04ec0ad628224f6
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637526B2

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