Water → (+/-)-4-(3-chlorophenyl)-6-[hydroxy[4-(hydroxymethyl)phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone

HRID 346991노트

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HRID 346991 반응식
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:35])([C:29]4[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=4)[C:21]4[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=4)[CH:18]=3)[N:13]([CH3:36])[C:12](=[O:37])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1.O>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:35])([C:21]4[CH:22]=[CH:23][C:24]([CH2:25][OH:26])=[CH:27][CH:28]=4)[C:29]4[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=4)[CH:18]=3)[N:13]([CH3:36])[C:12](=[O:37])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10299684(+/-)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde

생성물 1

HCID 10140969(+/-)-4-(3-chlorophenyl)-6-[hydroxy[4-(hydroxymethyl)phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

NaBH4 (0.00413 mol) was added portionwise at 0° C. to a mixture of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6 quinolinyl]hydroxy (1-methyl-1H-imidazol-5yl)methyl]benzaldehyde (described in Example B6).(0.00207 mol) in THF (10 ml). The mixture was stirred at 0° C. for 30 minutes, poured out into H2O and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 90/10/0.5; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.5 g (50%) of (±)-4-(3-chlorophenyl)-6-[hydroxy[4-(hydroxymethyl)phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone, mp. 273° C.

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue (0.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 90/10/0.5; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-92d2832ce3ac4c5aaa0a3836cd2b1b59
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173040B2

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