1,2-Dichloroethane → 4-[5-({(3S)-4-[(4-Chlorophenyl)sulfonyl]-3-methyl-1-piperazinyl}carbonyl)-2-pyridinyl]morpholine

HRID 2066121

Reaktionsgleichung

Reaktionsgleichung von HRID 2066121
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]2[CH3:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[N:33]1([C:39]2[N:44]=[CH:43][C:42]([C:45](O)=[O:46])=[CH:41][CH:40]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(N1CCOCC1)C>C(Cl)Cl.O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:45]([C:42]3[CH:41]=[CH:40][C:39]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[N:44][CH:43]=3)=[O:46])[CH2:14][C@@H:13]2[CH3:18])(=[O:10])=[O:11])=[CH:7][CH:8]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27764606-Morpholinonicotinic AcidHCID 67028562(2S)-1-[(4-Chlorophenyl)sulfonyl]-2-methylpiperazine hydrochloride

Produkt 1

HCID 591613674-[5-({(3S)-4-[(4-Chlorophenyl)sulfonyl]-3-methyl-1-piperazinyl}carbonyl)-2-pyridinyl]morpholineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of (2S)-1-[(4-chlorophenyl)sulfonyl]-2-methylpiperazine hydrochloride (Description 4) (105 mg, 0.338 mmol), EDC (71.3 mg, 0.372 mmol), HOBT.H2O (56.9 mg, 0.372 mmol) and 6-(4-morpholinyl)-3-pyridinecarboxylic acid (77 mg, 0.372 mmol) in DCM (5 ml) was added N-ethyl morpholine (0.090 mL, 0.710 mmol). The reaction was stirred for 18 h at ambient temperature. To the reaction was added water (3 ml) and the organic layer collected via a hydrophobic frit. The organic layer was reduced in volume to approximately 2 ml then loaded onto a silica SP4 chromatography cartridge. The cartridge was eluted with a gradient from 60% ethyl acetate in iso-hexane to ethyl acetate then ethyl acetate. Fractions containing the desired product were combined and reduced in vacuo to yield the title compound as a white solid (88 mg).

Aufarbeitung

  1. customthe organic layer collected via a hydrophobic frit
  2. washThe cartridge was eluted with a gradient from 60% ethyl acetate in iso-hexane to ethyl acetate
  3. additionFractions containing the desired product

Quellen und Nachweise

ORD-Eintrag
ord-eec7617ca1c8493a8a858850107fb276
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288388B2

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