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

HRID 2267517Notes

Reaction equation

HRID 2267517 reaction equation
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[CH:32]=[CH:31][S:30][CH:29]=4)[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11].[CH3:36][NH:37][CH3:38].C1COCC1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>>[CH3:36][N:37]([CH3:38])[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[CH:32]=[CH:31][S:30][CH:29]=4)[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11]

Participants

7

Reactant 6

HCID 674DimethylamineHCID 5238Sodium IodideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 82267SulfamideHCID 590032813-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 115619483-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamideYield 30%

Procedure

Following the general procedure for aminosulfonamide formation outlined in example 2, 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide (50 mg, 0.12 mmol) and 2M dimethyl amine in THF (0.3 mL, 0.60 mmol) were allowed to react in the presence of K2CO3 (84.6 mg, 0.24 mmol) and NaI (Cat. 5 mg). 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 (17.1 mg, 30%).

Workup

  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)

Sources & evidence

ORD record
ord-fcd8f0a43afc4b1a832f9f13fe777f14
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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