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

HRID 2267538Notes

Reaction equation

HRID 2267538 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].[NH:36]1[CH2:41][CH2:40][CH:39]([OH:42])[CH2:38][CH2:37]1.C([O-])([O-])=O.[K+].[K+]>>[OH:42][CH:39]1[CH2:40][CH2:41][N:36]([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[CH:32]=[CH:31][S:30][CH:29]=5)[CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:37][CH2:38]1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 82267SulfamideHCID 590032813-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 590033323-(1-{[3-(4-hydroxy-1-piperidinyl)propyl]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-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide (40 mg, 0.13 mmol) and 4-piperidinol (0.068 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 (8.2 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-b7a23e2a486a4b4cbcaba2c597cb5d7a
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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