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

HRID 474323ノート

反応式

HRID 474323 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-41207d98790c41d3a04ec0ad628224f6
出典データセット
uspto-grants-2014_01
特許番号
US08637526B2

反応ノート

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