Sodium Iodide → HCID 11526363, compound

HRID 2267543Notes

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

Participants

Reactant 5

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 31268Pyrrolidine

HCID 82267Sulfamide

HCID 687913173-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(4-fluorophenyl)-1H-indole-7-carboxamide

Product 1

HCID 11526363HCID 11526363, compoundYield 23%

Procedure

Following the general procedure for aminosulfonamide formation outlined in example 2, 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(4-fluorophenyl)-1H-indole-7-carboxamide (0.059 mmol) and pyrrolidine (0.025 mL, 0.295 mmol) were allowed to react in the presence of K2CO3 (37 mg, 0.118 mmol) and NaI (Cat. 2 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 (6.9 mg, 23%).

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-1a81e51268b6460880965fbe2c5fcaf0
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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