2-Methylbenzenesulfonamide → 2-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxy-N-[(2-methylphenyl)sulfonyl]benzamide

HRID 915598Notes

Reaction equation

HRID 915598 reaction equation
[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:14]=3[C:15](O)=[O:16])=[CH:10][C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:30]1([CH3:40])[C:31]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C.O>[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:14]=3[C:15]([NH:39][S:36]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH3:40])(=[O:37])=[O:38])=[O:16])=[CH:10][C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 69242-MethylbenzenesulfonamideHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 103400462-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxybenzoic acid

Product 1

HCID 589586262-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxy-N-[(2-methylphenyl)sulfonyl]benzamideYield 10%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxybenzoic acid (Example 29) (100 mg, 0.26 mmol) in dichloromethane (3 mL) were added o-toluenesulfonamide (53.3 mg, 0.31 mmol), EDCI (99.47 mg, 0.52 mmol), DMAP (63.40 mg, 0.52 mmol), and triethylamine (0.127 mL, 0.91 mmol). The reaction mixture was stirred for 2 h, and then diluted with dichloromethane (10 mL) and water (20 mL). The organic phase was separated and then washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography using 90% EtOAc/hexane, to afford the product (13.9 mg, 10.0%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.56 (s, 3H), 3.74 (s, 3H) 6.67 (s, 1H), 7.03 (dd, 2H), 7.26-7.60 (m, 14H), 7.84 (dd, 2H), 7.94 (d, 1H). ES-MS m/z 539.1 (MH+); HPLC RT (min) 3.71.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-8bb9175eff5f415988406bab711442fa
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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