2-Methylbenzenesulfonamide → HCID 9986282, compound

HRID 1975414Notes

Reaction equation

HRID 1975414 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22](=[O:32])[NH:23][CH2:24][CH:25]([CH3:31])[CH2:26][C:27]([F:30])([F:29])[F:28])[CH:20]=2)[N:15]([CH3:33])[CH:14]=1)[C:6]([OH:8])=O.[CH3:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[S:41]([NH2:44])(=[O:43])=[O:42]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22](=[O:32])[NH:23][CH2:24][CH:25]([CH3:31])[CH2:26][C:27]([F:28])([F:30])[F:29])[CH:20]=2)[N:15]([CH3:33])[CH:14]=1)[C:6]([NH:44][S:41]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[CH3:34])(=[O:42])=[O:43])=[O:8]

Participants

5

Reactant 2

HCID 69242-MethylbenzenesulfonamideHCID 100499743-Methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]benzoic acid

Product 1

HCID 9986282HCID 9986282, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-yl-methyl]benzoic acid (250 mg), 4-dimethylaminopyridine (69.8 mg), I-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (127 mg) and 2-methylbenzenesulfonamide (95.4 mg) in methylene chloride (5 mL) was stirred under a nitrogen atmosphere 4or 24 hours. The mixture was diluted with methylene chloride, washed (10% (w/v) hydrochloric acid, water), and evaporated. The resulting rose-colored foam was dissolved in methylene chloride (5 mL), filtered through a 0.45 micron membrane filter, and precipitated by addition to hexane (50 mL). The solid was collected by filtration to give the title compound (189.2 mg, 57%) as a pale pink powder; mp 147°-149° C. Analysis for C31H32F3N3O5S: Calculated: C, 60.48; H, 5.24; N, 6.83. Found: C, 60.39; H, 5.60; N, 6.59.

Workup

  1. washwashed (10% (w/v) hydrochloric acid, water)
  2. customevaporated
  3. dissolutionThe resulting rose-colored foam was dissolved in methylene chloride (5 mL)
  4. filtrationfiltered through a 0.45 micron membrane
  5. filtrationfilter
  6. customprecipitated by addition to hexane (50 mL)
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-a27532563c8548cf96719fd0d3b62ab9
Source dataset
uspto-grants-1994_02
Patent number
US05286740

Reaction notes

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