Hydrochloric Acid → 5-(N-methylaminomethyl)-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole

HRID 1167574Notes

Reaction equation

HRID 1167574 reaction equation
[CH:1]([NH:3][CH2:4][C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:6]=1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)=O.B.Cl>O1CCCC1>[CH3:1][NH:3][CH2:4][C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[C:6]=1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 220373995-(N-formylaminomethyl)-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole

Product 1

HCID 220374715-(N-methylaminomethyl)-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 5-(N-formylaminomethyl)-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole (8.74 g, 29.5 mmol) in 90 mL anhydrous tetrahydrofuran was added a 1.0 M solution of borane in tetrahydrofuran (90 mL, 90 mmol) and the mixture was stirred at room temperature for 24 h. 1 N aqueous hydrochloric acid (100 mL) was then added to this mixture and the solution was refluxed for 5 hours and cooled to room temperature. The solution was extracted with ether (2×250 mL) and the pH of the aqueous layer adjusted to 9 by addition of concentrated ammonium hydroxide. The aqueous layers (pH˜9) were then extracted with ethyl acetate (4×150 mL). The organic extracts were dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was triturated with acetonitrile and filtered to obtain the title compound as a white solid: MS (M+H): 283 (base peak).

Workup

  1. temperaturethe solution was refluxed for 5 hours
  2. temperaturecooled to room temperature
  3. extractionThe solution was extracted with ether (2×250 mL)
  4. additionthe pH of the aqueous layer adjusted to 9 by addition of concentrated ammonium hydroxide
  5. extractionThe aqueous layers (pH˜9) were then extracted with ethyl acetate (4×150 mL)
  6. dry with materialThe organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure
  9. customThe residue was triturated with acetonitrile
  10. filtrationfiltered

Sources & evidence

ORD record
ord-8c95c8c1e60b4bb4bdec764025d1f69d
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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