Pyridine → HCID 69629681, compound

HRID 1792841Notes

Reaction equation

HRID 1792841 reaction equation
Cl.NC(C[C:18]1[CH:26]=[C:25]([Cl:27])[C:24]([O:28][CH3:29])=[C:23]2[C:19]=1[CH:20]=[N:21][N:22]2[S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])C(NCCCCC1C=CC=CC=1)=O.[C:39]1([S:45](Cl)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[N:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>ClCCl.CCOC(C)=O>[C:39]1([S:45]([NH:22][CH:23]([CH2:19][C:20]2[C:19]3[C:23](=[C:24]([O:28][CH3:29])[C:25]([Cl:27])=[CH:26][CH:18]=3)[N:22]([S:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)(=[O:31])=[O:32])[N:21]=2)[C:24]([NH:49][CH2:54][CH2:53][CH2:52][CH2:51][C:50]2[CH:37]=[CH:38][CH:33]=[CH:34][CH:35]=2)=[O:28])(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 22025329HCID 22025329, compound

Product 1

HCID 69629681HCID 69629681, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-3-(1-benzenesulfonyl-6-chloro-7-methoxy-1H-indazol-4-yl)-N-(4-phenyl-butyl)-propionamide hydrochloride (0.31 g, 0.54 mmol) is dissolved in a mixture of dichloromethane (4 mL) and pyridine (1.5 mL). Benzenesulfonyl chloride (0.12 mL, 0.9 mmol) is added portionwise and the reaction is allowed to stir for a total of 18 h. The reaction is diluted with EtOAc and washed with water, 1N HCl three times, water, brine and dried over MgSO4. The solution is concentrated and purified by column chromatography (silica, 5% EtOAc/CH2Cl2 to provide 2-benzenesulfonylamino-3-(1-benzenesulfonyl-6-chloro-7-methoxy-1H-indazolyl)-N-(4-phenyl-butyl)-propionamide.

Workup

  1. washwashed with water, 1N HCl three times, water, brine
  2. dry with materialdried over MgSO4
  3. concentrationThe solution is concentrated
  4. custompurified by column chromatography (silica, 5% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-0dd0762a70394299b19c9382db300680
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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