Toluene → Isopropyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

HRID 1478275노트

반응식

HRID 1478275 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.[CH:17]([O:20][C:21](Cl)=[O:22])([CH3:19])[CH3:18].C1(C)C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[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:21]([O:20][CH:17]([CH3:19])[CH3:18])=[O:22])[CH2:13][CH2:12]3)=[N:7][C:6]=12

참가 물질

6

반응물 4

HCID 1140TolueneHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 866974343-Bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine

생성물 1

HCID 86697433Isopropyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine (2.5 g, 8.87 mmol) taken up in DCM. Isopropylchloroformate 1M in toluene (13.3 mL, 13.3 mmol), and triethylamine (2.47 mL, 17.7 mmol) added and stirred at room temperature 30 minutes. Reaction washed with water, DCM layer dried over magnesium sulfate filtered reduced in vacuo. Run on an Isco silica column with DCM:MeOH 0-5%. Product fractions were combined and reduced in vacuo to obtain 2.86 g crude product for further reaction as is. LRMS (ESI) m/z 368/370 [(M+H)]+, calc'd for C14H18BrN5O: 368.24.

후처리

  1. customReaction
  2. washwashed with water, DCM layer
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered

출처 및 근거

ORD 기록
ord-c8f83ad05944413398d97c63a69ee852
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403832B2

반응 노트

불러오는 중…