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

HRID 2267520Notes

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[S:28][CH:29]=[CH:30][CH:31]=4)[CH:25]=3)[NH:20][CH:19]=2)[CH2:14][CH2:13]1)(=[O:11])=[O:10].[CH:35]1([NH2:40])[CH2:39][CH2:38][CH2:37][CH2:36]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>>[CH:35]1([NH:40][CH2:7][CH2:8][S:9]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[C:26]4[C:21](=[C:22]([C:32]([NH2:34])=[O:33])[CH:23]=[C:24]([C:27]5[S:28][CH:29]=[CH:30][CH:31]=5)[CH:25]=4)[NH:20][CH:19]=3)[CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

Reactant 5

HCID 2906Cyclopentylamine

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 82267Sulfamide

HCID 687940633-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-(2-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 115696053-(1-{[2-(cyclopentylamino)ethyl]sulfonyl}-4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamideYield 39%

Procedure

Following the general procedure for aminosulfonamide formation outlined in example 2, 3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-(2-thienyl)-1H-indole-7-carboxamide (0.09 mmol) and cyclopentanamine (0.04 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 (14 mg, 39%).

Workup

customThe resulting residue was purified by reverse phase HPLC
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-0d87731c9161468eaa32c990a5670a0b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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