2-Methoxyethyl chloroformate → 2-Methoxyethyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

HRID 1478273노트

반응식

HRID 1478273 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:17](Cl)(=[O:23])[O:18][CH2:19][CH2:20][O:21][CH3:22]>CCOC(C)=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:17]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[O:23])[CH2:13][CH2:12]3)=[N:7][C:6]=12

참가 물질

4

반응물 2

HCID 694002-Methoxyethyl chloroformateHCID 866974343-Bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine

생성물 1

HCID 866974402-Methoxyethyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To 10.00 g (35.44 mmol) of 3-bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine dissolved in 120 mL of EtOAc, at 0° C. was added 5.40 g (38.99 mmol) of 2-methoxyethyl carbonochloridate, followed by 9.86 mL (70.88 mmol) of TEA. After 5 minutes, the ice bath was removed, and the reaction mixture stirred at RT. After 5 hr, LCMS showed that the reaction was complete. It was diluted with EtOAc, quenched with brine, and the organic layer dried over MgSO4. It was concentrated and purified on the ISCO with a 330 g column eluting with 0-9% MeOH/DCM to obtain the desired product, 12.63 g (93%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.42 (s, 3 H) 3.62-3.69 (m, 6 H) 3.73-3.82 (m, 4 H) 4.26-4.35 (m, 2 H) 6.36 (d, J=7.83 Hz, 1 H) 7.86 (s, 1 H) 8.27 (d, J=7.83 Hz, 1 H). LRMS (ESI) m/e 384 [(M+H)+, (doublet), calcd for C14H18BrN5O3 383].

후처리

  1. customthe ice bath was removed
  2. waitAfter 5 hr
  3. additionIt was diluted with EtOAc
  4. customquenched with brine
  5. dry with materialthe organic layer dried over MgSO4
  6. concentrationIt was concentrated
  7. custompurified on the ISCO with a 330 g column
  8. washeluting with 0-9% MeOH/DCM

출처 및 근거

ORD 기록
ord-27ea54ea42d04c69813262c3d981f6dd
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403832B2

반응 노트

불러오는 중…