HCID 61129737, compound → HCID 178464667, compound

HRID 1484443Notes

Reaction equation

HRID 1484443 reaction equation
CS[C:3]([N:7]1[CH2:11][C:10]([CH3:13])([CH3:12])[CH:9]=[N:8]1)=[N:4][CH2:5][CH3:6].[Br:14][C:15]1[CH:20]=[C:19]([S:21](=[O:24])(=[O:23])[NH2:22])[CH:18]=[CH:17][C:16]=1[NH:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28]>C(#N)C>[Br:14][C:15]1[CH:20]=[C:19]([S:21](=[O:24])(=[O:23])[N:22]=[C:3]([N:7]2[CH2:11][C:10]([CH3:12])([CH3:13])[CH:9]=[N:8]2)[NH:4][CH2:5][CH3:6])[CH:18]=[CH:17][C:16]=1[NH:25][C:26](=[O:31])[C:27]([F:29])([F:30])[F:28]

Participants

4

Reactant 2

HCID 61129737HCID 61129737, compoundHCID 67359253HCID 67359253, compound

Product 1

HCID 178464667HCID 178464667, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.41 g (1 mol equiv.) N-Ethyl-4,4-dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester and 6.24 g (1.05 mol equiv.) N-(2-Bromo-4-sulfamoyl-phenyl)-2,2,2-trifluoro-acetamide were added to 100 mL acetonitrile. The reaction mixture was refluxed overnight, and subsequently volatiles were removed under reduced pressure. The residue was taken up in ethyl acetate and extracted with 2N NaOH, and the organic layer was dried over Na2SO4, filtered and evaporated to dryness. Purification by flash chromatography on silica gel (Et2O) afforded 7.1 g (83%) N-(2-bromo-4-{[(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-sulfamoyl}-phenyl)-2,2,2-trifluoro-acetamide. 1H NMR (400 MHz, CDCl3) δ 1.18 (t, J=7.3 Hz, 3H), 1.24 (s, 6H), 3.43-3.51 (m, 2H), 3.79 (br.s., 2H), 6.78 (s, 1H), 7.93 (dd, J=8.6, 2.0 Hz, 1H), 8.19 (d, J=2.0 Hz, 1H), 8.39 (d, J=8.6 Hz, 1H), 8.61 (br.s., 1H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customsubsequently volatiles were removed under reduced pressure
  3. extractionextracted with 2N NaOH
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography on silica gel (Et2O)

Sources & evidence

ORD record
ord-7a47d23b32144387a51f15975c4879dc
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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