Sodium Iodide → HCID 11505484, compound

HRID 2267551Notes

Reaction equation

HRID 2267551 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].[NH2:37][CH:38]1[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>>[NH2:36][C:34]([C:23]1[CH:24]=[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[C:27]2[C:22]=1[NH:21][CH:20]=[C:19]2[CH:16]1[CH2:17][CH2:18][N:13]([S:10]([CH2:9][CH2:8][CH2:7][NH:37][CH:38]2[CH2:39][CH2:40][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:42][CH2:43]2)(=[O:12])=[O:11])[CH2:14][CH2:15]1)=[O:35]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 82267SulfamideHCID 12682914-Amino-1-Boc-piperidineHCID 590032803-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

Product 1

HCID 11505484HCID 11505484, compoundYield 26%

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 (50 mg, 0.0.109 mmol) and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (108.8 mg, 0.543 mmol) were allowed to react in the presence of K2CO3 (60 mg, 0.435 mmol) and sodium iodide (2 mg). The reaction mixture was concentrated under reduced pressure. 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 (17.3 mg, 26%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by reverse phase HPLC
  3. 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-ce09bd0eda4c44bba2faad29ef327372
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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