Acetic Acid → (+/-)-4-(3-chlorophenyl)-6-[hydroxy[4[[(2-methoxyethyl)amino]methyl]phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)quinolinone

HRID 346992노트

반응식

HRID 346992 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:33])([C:27]4[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=4)[C:19]4[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=4)[CH:16]=3)[N:11]([CH3:34])[C:10](=[O:35])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:36][O:37][CH2:38][CH2:39][NH2:40].C(O)(=O)C.[BH3-]C#N.[Na+]>C(#N)C.CCOC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:33])([C:19]4[CH:20]=[CH:21][C:22]([CH2:23][NH:40][CH2:39][CH2:38][O:37][CH3:36])=[CH:25][CH:26]=4)[C:27]4[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=4)[CH:16]=3)[N:11]([CH3:34])[C:10](=[O:35])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 5003444Sodium cyanoborohydrideHCID 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 21082094(+/-)-4-(3-chlorophenyl)-6-[hydroxy[4[[(2-methoxyethyl)amino]methyl]phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)quinolinone수율 7.13%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde (described in Example B6) (0.000207 mol), 2-methoxy-ethanamine (0.000517 mol) and acetic acid (0.0000207 mol) in acetonitrile (2 ml) was stirred at room temperature for 2 hours. NaBH3CN (0.000517 mol) was added and the resulting mixture was stirred at room temperature overnight. After addition of water and extraction with EtOAc, the solvent was evaporated. The residue was purified by HPLC. The product fractions were collected and the solvent was evaporated, yielding 0.008 g (7.13%) of (±)-4-(3-chlorophenyl)-6-[hydroxy[4[[(2-methoxyethyl)amino]methyl]phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)quinolinone, MS (ESI) m/z:543, 545 (MH+).

후처리

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customthe solvent was evaporated
  3. customThe residue was purified by HPLC
  4. customThe product fractions were collected
  5. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-e4c3f18eab614cada8ec7de14069a144
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173040B2

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