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

HRID 1844358
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HRID 1844358 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane
용매
2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ffa211f09b44b8c9c6eefdd34c6cf47
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08946415B2

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