Dimethylamine → 3-(1-{[2-(dimethylamino)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide

HRID 2267524Notes

Reaction equation

HRID 2267524 reaction equation
NS(N)(=O)=O.Cl[CH2:7][CH2:8][S:9]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[C:26]3[C:21](=[C:22]([C:32]([NH2:34])=[O:33])[CH:23]=[C:24]([C:27]4[CH:31]=[CH:30][S:29][CH:28]=4)[CH:25]=3)[NH:20][CH:19]=2)[CH2:14][CH2:13]1)(=[O:11])=[O:10].[CH3:35][NH:36][CH3:37].C1COCC1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>>[CH3:35][N:36]([CH3:37])[CH2:7][CH2:8][S:9]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[C:26]3[C:21](=[C:22]([C:32]([NH2:34])=[O:33])[CH:23]=[C:24]([C:27]4[CH:31]=[CH:30][S:29][CH:28]=4)[CH:25]=3)[NH:20][CH:19]=2)[CH2:14][CH2:13]1)(=[O:11])=[O:10]

Participants

7

Reactant 6

HCID 674DimethylamineHCID 5238Sodium IodideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 82267SulfamideHCID 687931013-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 115978023-(1-{[2-(dimethylamino)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamideYield 13%

Procedure

Following the general procedure for aminosulfonamide formation outlined in example 2, 3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide (0.09 mmol) and 2M dimethyl amine in THF (0.225 mL, 0.45 mmol) were allowed to react in the presence of K2CO3 (44 mg, 0.45 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 (5.5 mg, 13%).

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-b84fc4f8f38f4427b7ef1d50a5da9e06
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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