Hydrazine → HCID 9901547, compound

HRID 1374703Notes

Reaction equation

HRID 1374703 reaction equation
NS(C1C=C(C=CC=1Cl)C(O[CH2:11][C:12]1[CH:17]=[CH:16][N:15]2[N:18]=[C:19]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:14]2[CH:13]=1)=O)(=O)=O.[NH2:38]N>C(O)C>[F:33][C:30]1[CH:31]=[CH:32][C:27]([C:19]2[C:20]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)=[C:14]3[CH:13]=[C:12]([CH2:11][NH2:38])[CH:17]=[CH:16][N:15]3[N:18]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 10187046HCID 10187046, compound2×

Product 1

HCID 9901547HCID 9901547, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[2-(4-Fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridin-5-yl]methyl 3-(aminosulfonyl)-4-chlorobenzoate (Example 17 106 mg, 0.23 mmol) is dissolved in ethanol (10 mL) and hydrazine (64 mg, 2 mmol) added. The solution is refluxed for 6 h and allowed to cool. A precipitate of phthalhydrazide is filtered off and the mother liquor concentrated to dryness. The crude solid is taken up in dilute hydrochloric acid (20 mL), and washed twice with ethyl acetate (15 mL) followed by basification with sodium hydroxide solution. The solution is extracted five times with dichloromethane (20 mL), dried (MgSO4) and concentrated to give a solid (43 mg). Purified by preparative TLC, eluting with ethyl acteate plus 2% methanol, to give the title compound, 23 mg. 1H NMR (d6-DMSO) δ 3.75 (s, 2H), 6.97 (d, J=7.3 Hz, 1H), 7.22 (t, J=8.9 Hz, 2H), 7.28 (d, J=5.9 Hz, 2H), 7.50 (dd, J=5.7, 8.4 Hz, 2H), 7.64 (s, 1H), 8.53 (d, J=5.7 Hz, 2H), 8.68 (d, J=7.2 Hz, 1H); APESI-MS m/z 319 (M+1)+.

Workup

  1. temperatureThe solution is refluxed for 6 h
  2. temperatureto cool
  3. filtrationA precipitate of phthalhydrazide is filtered off
  4. concentrationthe mother liquor concentrated to dryness
  5. washwashed twice with ethyl acetate (15 mL)
  6. extractionThe solution is extracted five times with dichloromethane (20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0b80381e379c4b4d913359980c6d7a20
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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