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 2407068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407068
[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

Komponenten

7

Edukt 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

Produkt 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-carboxamideAusbeute 1.582,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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, 1H), 8.27 (t, 1H), 7.41 (dd, 1H), 7.29 (d, 1H), 7.15 (d, 1H), 6.97 (d, 1H), 6.96 (s, 1H), 6.83 (d. 1H), 3.83 (d, 1H), 3.57 (dd, 1H), 3.26 (q, 2H), 2.84 (m, 4H), 2.73 (dt, 1H), 2.40 (t, 2H), 2.20 (s, 3H), 2.00 (m, 1H), 1.83 (m, 1H), 1.69 (m, 3H), 1.52-1.33 (m, 3H). MS (ESI+) M/z: 496, 498 (M+H).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dbb45e41f098407a8b177beb0cb8177c
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809530B1

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