Sodium Iodide → HCID 11705934, compound

HRID 2267515Notes

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[CH2:41][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[CH2:41][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 11430Potassium Carbonate

HCID 31268Pyrrolidine

HCID 82267Sulfamide

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

Product 1

HCID 11705934HCID 11705934, compoundYield 42%

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 (60 mg, 0.13 mmol) and pyrrolidine (46.2 mg, 0.65 mmol) were allowed to react in the presence of K2CO3 (77 mg, 0.56 mmol) and NaI (Cat. 2.13 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 (27 mg, 42%).

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-562e494d9ec04bf8a1462a59b9f72146
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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