Sodium Iodide → HCID 59003343, compound

HRID 2267536Notes

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].[CH3:37][C@@H:38]1[CH2:42][CH2:41][C@@H:40]([CH3:43])[NH:39]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>>[CH3:37][C@@H:38]1[CH2:42][CH2:41][C@@H:40]([CH3:43])[N:39]1[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]

Participants

Reactant 5

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 82267Sulfamide

HCID 6417672,5-Dimethylpyrrolidine, (2R,5R)-

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

Product 1

HCID 59003343HCID 59003343, compoundYield 37%

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 (100 mg, 0.313 mmol) and (2R,5R)-2,5-dimethylpyrrolidine (449 mg, 1.56 mmol) were allowed to react in the presence of K2CO3 (886 mg, 0.63 mmol) and NaI (251 mg, 1.56 mmol). 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 (60 mg, 37%).

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-6b3fb93cfa2e4a1b8bbc1107e4805fd7
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

Loading…