Cyanogen Bromide → 4-(3-Bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carbonitrile

HRID 1478278ノート

反応式

HRID 1478278 の反応式
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][C:6]=12.C(=O)(O)[O-].[Na+].[N:22]#[C:23]Br>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:23]#[N:22])[CH2:13][CH2:12]3)=[N:7][C:6]=12

参加物

6

反応物 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 866974343-Bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine

生成物 1

HCID 866974444-(3-Bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

3-bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine (500 mg, 1.77 mmol) taken up in 20 mL DCM and stirred at 0° C. in an ice bath. Sodium bicarbonate (744 mg, 8.86 mmol) in 6 mL water added and stirred. Cyanogen bromide (225 mg, 2.12 mmol) added and stirred at 0° C. for 30 minutes then allowed to reach room temperature and stirred overnight. Reaction diluted with DCM washed with water, DCM layer dried over magnesium sulfate reduced in vacuo for 500 mg crude product for further reaction as is. LRMS (ESI) m/z 307/309 [(M+H)]+, calc'd for C11H11BrN6: 307.15.

後処理

  1. stirringstirred
  2. stirringstirred at 0° C. for 30 minutes
  3. customto reach room temperature
  4. stirringstirred overnight
  5. customReaction
  6. washwashed with water, DCM layer
  7. dry with materialdried over magnesium sulfate
  8. customreduced in vacuo for 500 mg crude product for further reaction

出典と根拠

ORDレコード
ord-71a8c1e670ec46c58069136eb98079c4
出典データセット
uspto-grants-2016_08
特許番号
US09403832B2

反応ノート

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