Triethylamine → (5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloro-2-oxoindolin-1-yl)methyl hexanoate

HRID 1971035

Reaktionsgleichung

Reaktionsgleichung von HRID 1971035
[C:1]([O:8][CH2:9]Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:11]1[CH:12]=[CH:13][C:14]2[S:19][N:18]=[C:17]([N:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][C:28]4[CH:29]=[C:30]5[CH2:38][C:36](=[O:37])[NH:35][C:31]5=[CH:32][C:33]=4[Cl:34])[CH2:22][CH2:21]3)[C:15]=2[CH:16]=1.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1.C.[Cl-].[Cl-]>[C:1]([O:8][CH2:9][N:35]1[C:31]2[C:30](=[CH:29][C:28]([CH2:27][CH2:26][N:23]3[CH2:24][CH2:25][N:20]([C:17]4[C:15]5[CH:16]=[CH:11][CH:12]=[CH:13][C:14]=5[S:19][N:18]=4)[CH2:21][CH2:22]3)=[C:33]([Cl:34])[CH:32]=2)[CH2:38][C:36]1=[O:37])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 60854ZiprasidoneHCID 525229Chloromethyl hexanoate

Produkt 1

HCID 49853879(5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloro-2-oxoindolin-1-yl)methyl hexanoateAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 20976018Dichloride methaneLösungsmittel

Versuchsvorschrift

Chloromethyl hexanoate (3.18 g, 19.0 mmol) in dichloromethane (6 mL) was added to a suspension of Ziprasidone free base (4.0 g, 9.6 mmol), triethyl amine (4.0 mL, 27 mmol) and 4-dimethylamino pyridine (DMAP, 0.708 g, 5 mmol) in dichloride methane (240 mL) at 25-30° C. The reaction solution was stirred for 24 h at same temperature. The crude mixture was washed with water (100 mL) followed by brine solution (100 mL), upon solvent evaporation under vacuum below 40° C. provided crude title product, Compound 322, which was further purified by silica gel column chromatography. (1.4 g, 27% yield).

Aufarbeitung

  1. washThe crude mixture was washed with water (100 mL)
  2. customfollowed by brine solution (100 mL), upon solvent evaporation under vacuum below 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-f4ac8a8616294365a5b79cf40b5c8df0
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431576B2

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