Water → HCID 178464658, compound

HRID 1484444Notes

Reaction equation

HRID 1484444 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8](=[O:22])(=[O:21])[N:9]=[C:10]([N:14]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH:16]=[N:15]2)[NH:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[NH:23]C(=O)C(F)(F)F.C(=O)([O-])[O-].[K+].[K+].O>CO>[NH2:23][C:3]1[CH:4]=[CH:5][C:6]([S:8]([N:9]=[C:10]([N:14]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH:16]=[N:15]2)[NH:11][CH2:12][CH3:13])(=[O:22])=[O:21])=[CH:7][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 178464667HCID 178464667, compound

Product 1

HCID 178464658HCID 178464658, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.0 g (1 mol equiv.) N-(2-Bromo-4-{[(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-sulfamoyl}-phenyl)-2,2,2-trifluoro-acetamide was dissolved in 225 mL methanol; 10.3 g (5 mol equiv.) potassium carbonate and 30 mL water were added and the reaction mixture was refluxed for 2.5 hours. Volatiles were evaporated under reduced pressure, and the residue was taken up in ethyl acetate and extracted with 2N NaOH. The organic layer was dried over Na2SO4, filtered and concentrated on silica gel. Purification by flash chromatography on silica gel (Et2O) afforded 4.1 g (73%) 4-amino-3-bromo-N-[(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-benzenesulfonamide. 1H NMR (400 MHz, CDCl3) δ 1.17 (t, J=7.3 Hz, 3H), 1.21 (s, 6H), 3.43-3.52 (m, 2H), 3.74 (br.s., 2H), 4.45 (br.s., 2H), 6.73 (s, 1H), 6.75 (d, J=8.4 Hz, 1H), 6.83-6.92 (br.s., 1H), 7.65 (dd, J=8.4, 2.0 Hz, 1H), 7.99 (d, J=2.0 Hz, 1H).

Workup

  1. temperaturethe reaction mixture was refluxed for 2.5 hours
  2. customVolatiles were evaporated under reduced pressure
  3. extractionextracted with 2N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated on silica gel
  7. customPurification by flash chromatography on silica gel (Et2O)

Sources & evidence

ORD record
ord-d93bf80b767149468deb7e7ce0c5107b
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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