Cesium carbonate → tert-butyl 4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate

HRID 555888노트

반응식

HRID 555888 반응식
F[C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[C:36]([C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=1)=[O:37].CN1CCCC1=O>O>[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[C:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][C:2]2[C:3]([CH:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)=[N:4][CH:5]=[CH:6][N:7]=2)=[CH:40][CH:39]=1)=[O:37]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanoneHCID 59351396Tert-butyl 4-(3-fluoropyrazin-2-yl)piperidine-1-carboxylate

생성물 1

HCID 59351389tert-butyl 4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

To a 350 mL pressure vial is added tert-butyl 4-(3-fluoropyrazin-2-yl)piperidine-1-carboxylate (200 mg, 0.711 mmol), Cs2CO3 (417 mg, 1.280 mmol), and (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (305 mg, 1.280 mmol) and N-methylpyrrolidinone (1.3 mL). The reaction was heated in the microwave at 150° C. 1 h. The reaction was added to a flask containing H2O (20 mL) with rapid stirring. The resulting slurry was filtered and the solid filter cake washed with H2O (3×5 mL). The solid was purified by ISCO (40 g SiO2, 0-20% MeOH/CH2Cl2) to give tert-butyl 4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate as a brown solid.

후처리

  1. custom1 h
  2. additionThe reaction was added to a flask
  3. filtrationThe resulting slurry was filtered
  4. filtrationthe solid filter cake
  5. washwashed with H2O (3×5 mL)
  6. customThe solid was purified by ISCO (40 g SiO2, 0-20% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-63d04538b8494a1c85be4e72e2a79890
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053438B2

반응 노트

불러오는 중…