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

HRID 2267518Notes

Reaction equation

HRID 2267518 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[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].[CH:36]1([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[CH:36]1([NH:41][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])[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 5

HCID 2906CyclopentylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 82267SulfamideHCID 590033233-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(2-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 117132743-(1-{[3-(cyclopentylamino)propyl]sulfonyl}-4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 (50 mg, 0.12 mmol) and cyclopentyl amine (54 uL, 0.60 mmol) were allowed to react in the presence of K2CO3 (74 mg, 0.55 mmol) and NaI (Cat. 5 mg) in DMF at 120° C. 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 (27.2 mg, 44%).

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-9cac0afb39fa489fb7c623f26aae84a7
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

Loading…