Morpholine → 3-(1-{[3-(4-morpholinyl)propyl]sulfonyl}-4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamide

HRID 2267540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2267540
NS(N)(=O)=O.Cl[CH2:7][CH2:8][CH2:9][S:10]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[C:23]([C:33]([NH2:35])=[O:34])[CH:24]=[C:25]([C:28]4[S:29][CH:30]=[CH:31][CH:32]=4)[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C([O-])([O-])=O.[K+].[K+]>>[N:36]1([CH2:7][CH2:8][CH2:9][S:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[C:27]4[C:22](=[C:23]([C:33]([NH2:35])=[O:34])[CH:24]=[C:25]([C:28]5[S:29][CH:30]=[CH:31][CH:32]=5)[CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Komponenten

5

Edukt 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 82267SulfamideHCID 590033233-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(2-thienyl)-1H-indole-7-carboxamide

Produkt 1

HCID 590033223-(1-{[3-(4-morpholinyl)propyl]sulfonyl}-4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamideAusbeute 57 %

Versuchsvorschrift

Following the general procedure for aminosulfonamide formation outlined in example 2, 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(2-thienyl)-1H-indole-7-carboxamide (40 mg, 0.13 mmol) and morpholine (0.069 mL, 0.65 mmol) were allowed to react in the presence of K2CO3 (74 mg, 0.65 mmol). The resulting residue was purified by reverse phase HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give the title compound (37.3 mg, 57%).

Aufarbeitung

  1. customThe resulting residue was purified by reverse phase HPLC
  2. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-824edcf2d7294d2daebd286859d1273c
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858796B2

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