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

HRID 474344ノート

反応式

HRID 474344 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ef4852d7f4724534a31a9dd1fca05b27
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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