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 576507노트

반응식

HRID 576507 반응식
[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

참가 물질

7

반응물 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

생성물 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-carboxamide수율 1,582.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-459c9a44f6934a6181d8336a339e1109
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040508B2

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