홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

1,1'-Carbonyldiimidazole → (R)-(3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidin-1-yl)(4,4-difluoropiperidin-1-yl)methanone

HRID 1969741
노트
인쇄 미리보기

반응식

HRID 1969741 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH2:3]1.C1N=CN([C:25]([N:27]2[CH:31]=N[CH:29]=[CH:28]2)=[O:26])C=1.Cl.[F:33][C:34]1([F:40])CCNC[CH2:35]1>N1C=CC=CC=1>[C:8]1([C@@H:4]2[CH2:5][CH2:6][CH2:7][N:2]([C:25]([N:27]3[CH2:28][CH2:29][C:34]([F:40])([F:33])[CH2:35][CH2:31]3)=[O:26])[CH2:3]2)[N:12]2[C:13]3[CH:19]=[CH:18][NH:17][C:14]=3[N:15]=[CH:16][C:11]2=[CH:10][N:9]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 682631,1'-Carbonyldiimidazole2회HCID 27583514,4-Difluoropiperidine hydrochlorideHCID 67216656(R)-1-(piperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride

생성물 1

HCID 58557191(R)-(3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidin-1-yl)(4,4-difluoropiperidin-1-yl)methanone수율 49.5%

시약·촉매·용매 1

HCID 1049
Pyridine
용매

반응 조건

온도
50 °C

실험 절차

To a solution of (R)-1-(piperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride (0.24 g, 0.76 mmol) in pyridine (7.2 mL) was added CDI (0.14 g, 0.87 mmol) and the reaction mixture was stirred at about 50° C. for about 2 h. Additional CDI (0.02 g, 0.14 mmol) was added and the reaction mixture was stirred for about 1 h. To the reaction mixture was added 4,4-difluoropiperidine hydrochloride (0.12 g, 0.76 mmol). The reaction mixture was heated to about 55° C. for about 1 h, cooled to ambient temperature, and stirred for about 2 d. The solvent was removed under reduced pressure and the crude residue dissolved with DCM (5 mL) and washed with water (2 mL). The aqueous layer was back extracted with DCM (2 mL). The combined organic extracts were washed with brine (3 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-5% MeOH in DCM to afford (R)-(3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidin-1-yl)(4,4-difluoropiperidin-1-yl)methanone (0.146 g, 49%) as an off white solid: LC/MS (Table 1, Method b) Rt=1.70 min; MS m/z: 389 (M+H)+.

후처리

  1. stirringthe reaction mixture was stirred for about 1 h
  2. temperatureThe reaction mixture was heated to about 55° C. for about 1 h
  3. temperaturecooled to ambient temperature
  4. stirringstirred for about 2 d
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe crude residue dissolved with DCM (5 mL)
  7. washwashed with water (2 mL)
  8. extractionThe aqueous layer was back extracted with DCM (2 mL)
  9. washThe combined organic extracts were washed with brine (3 mL)
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. customThe crude material was purified by silica gel chromatography
  13. washeluting with a gradient of 0-5% MeOH in DCM

출처 및 근거

ORD 기록
ord-a5a5e04237d642bc8256814e749c3ea5
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08426411B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트