4-Nitrophenyl chloroformate → (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate

HRID 643153노트

반응식

HRID 643153 반응식
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[CH2:14]([O:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH2:29][C@@H:30]([OH:35])[C:31]([O:33][CH3:34])=[O:32])=[CH:24][C:23]=1[CH3:36])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:37]1[CH2:42][CH2:41][CH:40]([N:43]2[C:47]3[CH:48]=[N:49][C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][C:55]=4[C:46]=3[NH:45][C:44]2=[O:56])[CH2:39][CH2:38]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:56]=[C:44]1[N:43]([CH:40]2[CH2:39][CH2:38][N:37]([C:2]([O:35][C@@H:30]([C:31]([O:33][CH3:34])=[O:32])[CH2:29][C:25]3[CH:24]=[C:23]([CH3:36])[C:22]([O:21][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:27]([CH3:28])[CH:26]=3)=[O:3])[CH2:42][CH2:41]2)[C:47]2[CH:48]=[N:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][C:55]=3[C:46]=2[NH:45]1

참가 물질

6

반응물 3

HCID 821294-Nitrophenyl chloroformateHCID 183215593-Piperidin-4-yl-1,3-dihydroimidazo[4,5-c]quinolin-2-oneHCID 67273374methyl(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate

생성물 1

HCID 68676084(R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매2회

실험 절차

Under a nitrogen atmosphere 1.28 g (6.36 mmol) 4-nitrophenyl chloroformate were added at RT to a solution of 0.78 g (6.36 mmol) 4-dimethylaminopyridine in 100 mL pyridine and the mixture was stirred for 1 h at RT. Then a solution of 2.00 g (6.36 mmol) methyl (R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate in 20 mL pyridine was added dropwise at RT and the reaction mixture was stirred for 2 h after the end of the addition. Then 1.71 g (6.36 mmol) 3-piperidin-4-yl-1,3-dihydro-imidazo[4,5-c]quinoline-2-one was added to the reaction mixture, which was then heated to 100° C. for 4 h. The precipitate formed was filtered off, the filtrate was evaporated down i.vac., the residue was mixed with 200 mL EtOAc and 200 mL semisaturated KHSO4 solution, the product being obtained as a precipitate. This was suction filtered and dried.

후처리

  1. stirringthe reaction mixture was stirred for 2 h
  2. additionafter the end of the addition
  3. temperaturewas then heated to 100° C. for 4 h
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. customthe filtrate was evaporated down i.vac
  7. addition, the residue was mixed with 200 mL EtOAc and 200 mL semisaturated KHSO4 solution
  8. customthe product being obtained as a precipitate
  9. filtrationThis was suction filtered
  10. customdried

출처 및 근거

ORD 기록
ord-8b38c85137d74a43a2fc2a9d1393bcd4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696209B2

반응 노트

불러오는 중…