Ethyl orthopropionate → tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate

HRID 9441

반응식

HRID 9441 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[CH:9][CH:8]=[C:7]([Br:27])[CH:6]=2.[C:28](OCC)(OCC)(OCC)[CH2:29][CH3:30]>>[Br:27][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][CH:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]4)[C:28]([CH2:29][CH3:30])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

참가 물질

3

반응물 2

HCID 66995Ethyl orthopropionateHCID 21984428Tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate

생성물 1

HCID 21984257tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate수율 77.1%

실험 절차

The method described in Part A of Examples 142–144 was used to treat tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate (15.0 g, 34.5 mmol) with triethyl orthopropionate (6.68 g, 37.9 mmol). After completion, the reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA) followed by recrystallization from ethyl acetate to provide 12.6 g of tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate as a white powder, mp 208–209° C.

후처리

  1. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA)
  3. customfollowed by recrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-9ba31f07c1b444a68ce2aed691763f55
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

연결된 노트

불러오는 중…