Sodium Iodide → HCID 11555269, compound

HRID 2267513Notes

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:34]([NH2:36])=[O:35])[CH:24]=[C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11].[NH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>>[C:28]1([C:25]2[CH:26]=[C:27]3[C:22](=[C:23]([C:34]([NH2:36])=[O:35])[CH:24]=2)[NH:21][CH:20]=[C:19]3[CH:16]2[CH2:17][CH2:18][N:13]([S:10]([CH2:9][CH2:8][CH2:7][N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)(=[O:12])=[O:11])[CH2:14][CH2:15]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Reactant 5

HCID 5238Sodium Iodide

HCID 8082Piperidine

HCID 11430Potassium Carbonate

HCID 82267Sulfamide

HCID 590032803-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

Product 1

HCID 11555269HCID 11555269, compoundYield 47.6%

Procedure

Following the general procedure for aminosulfonamide formation outlined in example 2, 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide (62 mg, 0.13 mmol) and piperidine (55.25 mg, 0.65 mmol) were allowed to react in the presence of K2CO3 (72 mg, 0.56 mmol) and NaI (Cat. 2.0 mg). The resulting residue 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 (31.5 mg, 46%).

Workup

customThe resulting residue 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-660e12d72d5649c59564a87854be29c6
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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