Hydrochloric Acid → HCID 59631633, compound

HRID 2369068Notes

Reaction equation

HRID 2369068 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25](=[O:28])(=[O:27])[NH2:26])[CH:20]=3)=[CH:17][CH:18]=2)=[CH:12][C:11]([C:29](OC)=[O:30])=[N:10]1.[F-].[K+].Cl.[CH:36]([OH:39])([CH3:38])[CH3:37]>>[NH2:26][S:25]([C:21]1[CH:20]=[C:19]([C:16]2[S:15][C:14]([C:13]3[N:9]([C:3]4[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=4[Cl:1])[N:10]=[C:11]([C:29]([O:39][CH:36]([CH3:38])[CH3:37])=[O:30])[CH:12]=3)=[CH:18][CH:17]=2)[CH:24]=[CH:23][CH:22]=1)(=[O:28])=[O:27]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 522689Potassium FluorideHCID 59632412HCID 59632412, compound

Product 1

HCID 59631633HCID 59631633, compound

Conditions

Temperature
82.5 °C

Procedure

Into a 25 mL flask was weighed 114 mg (224 mmol) of methyl 1-(2,5-dichlorophenyl)-5-(5-(3-sulfamoylphenyl)thiophen-2-yl)-1H-pyrazole-3-carboxylate, 156 mg of KF, 4 mL of isopropyl alcohol, and 200 μL of concentrated HCl. The reaction was heated at 80-85° C. for 3 days. The reaction was then washed into a separatory funnel with ethyl acetate and water. The ethyl acetate was separated, washed with brine, was dried (Na2SO4), and concentrated in vacuo. Product was further purified by silica gel flash chromatography (Jones Flashmaster, 25 g SiO2, gradient elution from 20% ethyl acetate to 60% ethyl acetate over 30 minutes). Appropriate fractions were combined and concentrated in vacuo to afford the product as a colorless powder, yield: 53.3 mg (44%). 1H NMR (400 MHz, CDCl3): δ 8.05 (s, 1H), 7.83 (d, J=8 Hz, 1H), 7.66 (d, J=8 Hz, 1H), 7.59 (s, 1H), 7.44-7.51 (m, 3H), 7.21 (d, J=4 Hz, 1H), 7.13 (s, 1H), 6.81 (d, J=4 Hz, 1H), 5.33 (heptet, J=6 Hz, 1H), 5.08 (s, 2H), 1.41 (d, J=7 Hz, 6H); MS (ES): 536 [M+H]+.

Workup

  1. customInto a 25 mL flask was weighed
  2. washThe reaction was then washed into a separatory funnel with ethyl acetate and water
  3. customThe ethyl acetate was separated
  4. washwashed with brine
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customProduct was further purified by silica gel flash chromatography (Jones Flashmaster, 25 g SiO2, gradient elution from 20% ethyl acetate to 60% ethyl acetate over 30 minutes)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a77e30a5f8f74222bfcd0903aaa4d3e7
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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