Potassium Carbonate → 5-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2267495
[NH2:1]S(N)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](C(N)=O)=[C:10]2[CH:19]1[CH2:24][CH2:23][N:22]([S:25]([CH2:28][CH2:29][CH2:30]Cl)(=[O:27])=[O:26])[CH2:21][CH2:20]1.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.[C:37]([O-:40])([O-])=O.[K+].[K+]>>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([C:37]([NH2:1])=[O:40])[CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:19]1[CH2:20][CH2:21][N:22]([S:25]([CH2:28][CH2:29][CH2:30][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)(=[O:27])=[O:26])[CH2:23][CH2:24]1

Komponenten

5

Edukt 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 82267SulfamideHCID 687912945-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indole-carboxamide

Produkt 1

HCID 590033005-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamideAusbeute 87 %

Versuchsvorschrift

Following the general procedure for aminosulfonamide formation outlined in example 2, 5-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indole-carboxamide (656 mg, 1.41 mmol) and pyrrolidine (505 mg, 7.05 mmol) were allowed to react in the presence of K2CO3 (389.16 mg, 2.82 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 (600 mg, 87%).

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-b8811802518042b1ae5e4a15f9a8935b
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858796B2

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