1,2-Dichloroethane → N-(3-(4-(5-chloro-2-methylphenyl)piperazin-1-yl)propyl)-6,6a,7,8,9,10-hexahydro-6-oxo-5H-pyrido[1,2-a]quinoxaline-3-carboxamide

HRID 576507ノート

反応式

HRID 576507 の反応式
[O:1]=[C:2]1[NH:11][C:10]2[CH:9]=[C:8]([C:12]([OH:14])=O)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:15][CH2:16][CH2:17][CH2:18][CH:3]12.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:36])=[C:24]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][NH2:35])[CH2:28][CH2:27]2)[CH:25]=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:36])=[C:24]([N:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][CH2:34][NH:35][C:12]([C:8]3[CH:7]=[CH:6][C:5]4[N:4]5[CH2:15][CH2:16][CH2:17][CH2:18][CH:3]5[C:2](=[O:1])[NH:11][C:10]=4[CH:9]=3)=[O:14])[CH2:30][CH2:31]2)[CH:25]=1

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 433253696-oxo-6,6a,7,8,9,10-hexahydro-5H-pyrido[1,2-a]quinoxaline-3-carboxylic acidHCID 441227473-[4-(5-Chloro-2-methylphenyl)piperazin-1-yl]propan-1-amine

生成物 1

HCID 20966565N-(3-(4-(5-chloro-2-methylphenyl)piperazin-1-yl)propyl)-6,6a,7,8,9,10-hexahydro-6-oxo-5H-pyrido[1,2-a]quinoxaline-3-carboxamide収率 1,582.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6,6a,7,8,9,10-hexahydro-6-oxo-5H-pyrido[1,2-a]quinoxaline-3-carboxylic acid (200 mg, 0.80 mmole), 3-(4-(5-chloro-2-methylphenyl)piperazin-1-yl)propan-1-amine (1.0 mmol), DMAP (10 mg) and DIPEA (0.30 mL) in DMF (5 mL) was added EDC (0.377 g, 2.0 mmole). The reaction solution was stirred at room temperature overnight. The solvent removed and EtOAc (60 mL) was added. The organic layer was washed with saturated sodium bicarbonate (10 mL), water (10 mL) and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified by column chromatography with 0-10% methanol in dichloromethane to provide the N-(3-(4-(5-chloro-2-methylphenyl)piperazin-1-yl)propyl)-6,6a,7,8,9,10-hexahydro-6-oxo-5H-pyrido[1,2-a]quinoxaline-3-carboxamide as white solid (6.28 g, 78%). 1HNMR (300 MHz, dmso-d6), ppm: 10.48 (s, 1 H), 8.27 (t, 1 H), 7.41 (dd, 1 H), 7.29 (d, 1 H), 7.15 (d, 1 H), 6.97 (d, 1 H), 6.96 (s, 1 H), 6.83 (d, 1 H), 3.83 (d, 1 H), 3.57 (dd, 1 H), 3.26 (q, 2 H), 2.84 (m, 4 H), 2.73 (dt, 1 H), 2.40 (t, 2 H), 2.20 (s, 3 H), 2.00 (m, 1 H), 1.83 (m, 1 H), 1.69 (m, 3 H), 1.52-1.33 (m, 3 H). MS (ESI+) M/z: 496, 498 (M+H).

後処理

  1. customThe solvent removed
  2. additionEtOAc (60 mL) was added
  3. washThe organic layer was washed with saturated sodium bicarbonate (10 mL), water (10 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by column chromatography with 0-10% methanol in dichloromethane

出典と根拠

ORDレコード
ord-459c9a44f6934a6181d8336a339e1109
出典データセット
uspto-grants-2015_05
特許番号
US09040508B2

反応ノート

読み込み中…