HCID 178494946, compound → HCID 178520602, compound

HRID 1095436Notes

Reaction equation

HRID 1095436 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]([N:32]2[CH2:36][CH:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:34]([C:43]3[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=3)=[N:33]2)[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)(OC)[O:21]C)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C1COCC1.CO.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]([N:32]2[CH2:36][CH:35]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:34]([C:43]3[CH:44]=[CH:45][C:46]([Cl:49])=[CH:47][CH:48]=3)=[N:33]2)[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[O:21])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178494946HCID 178494946, compound

Product 1

HCID 178520602HCID 178520602, compoundYield 115.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Part B: 4-Chloro-N-{[3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-[7-(4-fluoro-phenyl)-7,7-dimethoxyheptylamino] methylene}-benzenesulfonamide (0.200 g, 0.258 mmol) was dissolved in a 1:1 mixture of THF/methanol (30 ml) and 1 N hydrochloric acid (5 ml) was added and the resulting mixture was stirred at room temperature for 20 hours. The mixture was quenched with 5% aqueous NaHCO3. Most of the THF and methanol were removed by evaporation in vacuo. The remaining water layer was twice extracted with ethylacetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The obtained crude 4-chloro-N-{[3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-[7-(4-fluorophenyl)-7-oxo-heptylamino] methylene}benzenesulfonamide (203 mg) was not further purified. Some characteristic aromatic 1H-NMR signals are: (400 MHz, CDCl3) δ 7.12 (d, J˜8, 2H), 7.22-7.33 (m, 5H) 7.39 (d, J˜8, 2H), 7.50 (d, J˜8, 2H), 7.72 (d, J˜8, 2H), 7.84 (d, J˜8, 2H), 8.05 (d, J˜8, 2H).

Workup

  1. additionwas added
  2. customThe mixture was quenched with 5% aqueous NaHCO3
  3. customMost of the THF and methanol were removed by evaporation in vacuo
  4. extractionThe remaining water layer was twice extracted with ethylacetate
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a336b73494f24ecd9602b237ce0c320a
Source dataset
uspto-grants-2012_03
Patent number
US08138174B2

Reaction notes

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