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 346992ノート

反応式

HRID 346992 の反応式
[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

参加物

8

反応物 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

生成物 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)quinolinone収率 7.13%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-e4c3f18eab614cada8ec7de14069a144
出典データセット
uspto-grants-2007_02
特許番号
US07173040B2

反応ノート

読み込み中…