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

HRID 2267516Notes

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[CH2:40][CH2:39][CH2:38][CH2:37]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>>[N:36]1([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])[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

Reactant 5

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 31268Pyrrolidine

HCID 82267Sulfamide

HCID 590032813-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 115116883-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamideYield 39%

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 (55 mg, 0.12 mmol) and pyrrolidine (42.6 mg, 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 (23.2 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-1ae465096c0c4cfd988cfc502908ce9c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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