2-Methylbenzenesulfonamide → HCID 44460797, compound

HRID 1739589Notes

Reaction equation

HRID 1739589 reaction equation
[F:1][CH:2]([F:33])[N:3]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([O:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:14])=[CH:9][CH:10]=2)[C:5]([CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][C:23]=2[O:31][CH3:32])=[CH:4]1.Cl.C(N=C=N)C.[C:40]1([CH3:50])[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[S:46]([NH2:49])(=[O:48])=[O:47].CO.C(Cl)Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:33][CH:2]([F:1])[N:3]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([O:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)=[O:14])=[CH:9][CH:10]=2)[C:5]([CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([NH:49][S:46]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[CH3:50])(=[O:47])=[O:48])=[O:28])=[CH:24][C:23]=2[O:31][CH3:32])=[CH:4]1

Participants

7

Reactant 4

HCID 69242-MethylbenzenesulfonamideHCID 21226129Dichloromethane methanolHCID 21883477Ethylcarbodiimide hydrochlorideHCID 54303394HCID 54303394, compound

Product 1

HCID 44460797HCID 44460797, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[1-difluoromethyl-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (1.10 grams, 2.37 mmol), 4-dimethylaminopyridine (0.44 grams, 3.63 mmol) and 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1,2-dichloroethane) (0.70 grams, 3.64 mmol) in methylene chloride (100 mL) was added o-tolylsulfonamide (0.41 grams, 2.42 mmol). The resulting solution was stirred for 16 hours at room temperature. The solution was diluted with methylene chloride and washed with 1 M hydrochloric acid (ag) and brine. The organics were dried over sodium sulfate and concentrated. Chromatography on silica gel (5% methanol/methylene chloride gave 4-[1-difluoromethyl-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-N-o-tolylsulfonylbenzamide (1.10 grams, 76% yield). HRMS calcd. for C31H31N3O6F2S: 611.1902. Found: 611.1924.

Workup

  1. washwashed with 1 M hydrochloric acid (ag) and brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ea3b957f02994b74816af891db9a60f0
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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