1-Cyclopropylethanol → [4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester

HRID 252609

반응식

HRID 252609 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:20]3[CH2:23][CH2:22][CH2:21]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([OH:19])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+]([O-])=O)=C[CH:29]=1)=[O:26].C1(C(C)O)CC1>N1C=CC=CC=1.Cl>[CH:33]1([CH:28]([O:27][C:25](=[O:26])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]([CH:20]4[CH2:21][CH2:22][CH2:23]4)[C:10]4[C:15]([C:16]=3[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([OH:19])[CH:11]=4)=[CH:4][CH:3]=2)[CH3:29])[CH2:32][CH2:31]1

참가 물질

6

반응물 3

HCID 791041-CyclopropylethanolHCID 821294-Nitrophenyl chloroformateHCID 497727192-(4-Aminophenyl)-1-cyclobutyl-6-hydroxy-indole-3-carbonitrile

생성물 1

HCID 59425704[4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester수율 80%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 1049Pyridine용매

실험 절차

To a solution of 2-(4-aminophenyl)-1-cyclobutyl-6-hydroxy-1H-indole-3-carbonitrile (909 mg, 3 mmol) in pyridine (5 mL) is added 4-nitrophenyl chloroformate (6 mmol) at room temperature and then stirred for 2 h at room temperature. To the reaction is added cyclopropyl methyl carbinol and then stirred for 8 h at 80° C. The reaction mixture is diluted with 1N HCl and then extracted with ethyl acetate. The organic layer is concentrated and the residue is dissolved in EtOAc and triturated with hexane. The precipitate is collected by filtration and washed with hexane and dried in vacuo to afford [4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester (996 mg, 80%).

후처리

  1. stirringstirred for 8 h at 80° C
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer is concentrated
  4. dissolutionthe residue is dissolved in EtOAc
  5. customtriturated with hexane
  6. filtrationThe precipitate is collected by filtration
  7. washwashed with hexane
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-d7904bb0a8d342eaa6b82260d1848e1d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868037B2

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