7-benzyloxy-1-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline → 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol

HRID 540884노트

반응식

HRID 540884 반응식
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH:23]4[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]4)[C:20]([CH2:30][O:31][CH2:32][CH3:33])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1>C(#N)C.C(Cl)(Cl)Cl.CO.[OH-].[Pd+2].[OH-]>[CH3:28][C:25]1([CH3:29])[O:24][CH:23]([CH2:22][N:21]2[C:13]3[C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=4[N:16]=[CH:15][C:14]=3[N:19]=[C:20]2[CH2:30][O:31][CH2:32][CH3:33])[CH2:27][O:26]1

참가 물질

5

반응물 1

HCID 670511477-benzyloxy-1-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline

생성물 1

HCID 1363478501-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol수율 93.4%

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 6342Acetonitrile용매HCID 21584188Chloroform methanol용매

실험 절차

Palladium hydroxide (Pearlman's catalyst) (20% wt. % palladium on carbon, 2.2 g) was added to a solution of 7-benzyloxy-1-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (22.2 g, 49.6 mmol) in acetonitrile (400 mL) and the reaction mixture was hydrogenated (30 psi, 2.1×105 Pa) for 24 hours on a Parr apparatus. The crude reaction mixture was diluted with 1:1 chloroform/methanol (1 L), then was filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure and triturated with acetonitrile. The resulting crystalline material was collected by filtration, washed with acetonitrile, and dried to afford 16.55 g of 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol as a white powder, mp 239-240° C.

후처리

  1. customfor 24 hours
  2. customThe crude reaction mixture
  3. filtrationwas filtered through a layer of CELITE filter agent
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customtriturated with acetonitrile
  6. filtrationThe resulting crystalline material was collected by filtration
  7. washwashed with acetonitrile
  8. customdried

출처 및 근거

ORD 기록
ord-a063aa88d01b4fa2a08a3d15677d386d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871782B2

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