Ethanol → HCID 53901480, compound

HRID 1379146Notes

Reaction equation

HRID 1379146 reaction equation
[CH3:1][O:2][C:3]1[C:12]([F:13])=[C:11]2[C:6]([C:7](=O)[CH:8]([C:14](=O)[C:15]([F:18])([F:17])[F:16])OC2)=[CH:5][CH:4]=1.[CH:21]1[C:26]([NH:27][NH2:28])=[CH:25][CH:24]=[C:23]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:22]=1.Cl.[CH2:34]([OH:36])C>>[F:13][C:12]1[C:11]2[O:36][CH2:34][C:8]3[C:14]([C:15]([F:16])([F:17])[F:18])=[N:28][N:27]([C:26]4[CH:21]=[CH:22][C:23]([S:29]([NH2:32])(=[O:30])=[O:31])=[CH:24][CH:25]=4)[C:7]=3[C:6]=2[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 3

HCID 702EthanolHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 54244781HCID 54244781, compound

Product 1

HCID 53901480HCID 53901480, compoundYield 30%

Procedure

7-Methoxy-8-fluoro-3-(trifluoroacetyl)isochroman-4-one from Step 3 (450 mg, 1.47 mmol) and 4-sulfonamidophenylhydrazine hydrochloride (430 mg, 1.92 mmol) were dissolved in 5 mL of anhydrous ethanol and heated to reflux for 45 minutes. The solution was concentrated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with 3N hydrochloric acid, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was crystallized from a mixture of isooctane and ethyl acetate to afford 4-[1,4-dihydro-6-fluoro-7-methoxy-3-(trifluoromethyl)-[1]benzopyrano[4,3-c]pyrazol-1-yl]benzenesulfonamide as a white solid (200 mg, 30%): mp 289.5°-291.0° C.; 1H NMR (acetone d6 /300 MHz) 8.12 (d, J=8.4 Hz, 2H), 7.90 (d, J=8.5 Hz. 2H), 7.07 (dd, J=8.7, 8.5 Hz, 1H), 6.83 (br s, 2H), 6.75 (d, J=8.7 Hz, 1H), 5.45 (s, 2H), 3.90 (s, 3H); 19F NMR (acetone d /282 MHz) -62.51 (s), -140.97 (d). High resolution mass spectrum Calc'd. for C18H13F4N3 O4S: 443.0563. Found: 443.0570.

Workup

  1. temperatureheated
  2. temperatureto reflux for 45 minutes
  3. concentrationThe solution was concentrated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was washed with 3N hydrochloric acid, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized from a mixture of isooctane and ethyl acetate

Sources & evidence

ORD record
ord-e8e2183e50234ce79d10b7f3bd491153
Source dataset
uspto-grants-1997_09
Patent number
US05670532

Reaction notes

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