Ammonium formate → HCID 135788276, compound

HRID 353282Notes

Reaction equation

HRID 353282 reaction equation
C([O-])=O.[NH4+].[NH2:5][C:6]1[N:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:9]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[CH:17][CH:16]=2)[C:7]=1[C:29]([NH2:31])=[O:30]>CO.C1COCC1.[Pd]>[NH2:5][C:6]1[N:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:9]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:7]=1[C:29]([NH2:31])=[O:30]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 22169797HCID 22169797, compound

Product 1

HCID 135788276HCID 135788276, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium formate (160 mg, 2.5 mmol) and 10% Pd/C (50 mg) are added to a solution of 21 (2 mmol) from the preceding reaction in methanol (4 mL) and THF (2 mL). The mixture is stirred at room temperature. The reaction is monitored by tlc and after reaction occurs, the mixture is filtered through Celite and rinsed with ethyl acetate. The filtrate is diluted with ethyl acetate and is washed successively with aq. NaHCO3 and with half-saturated brine, then dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The desired 5-amino-1-(1,1-dimethylethyl)-3-(4-hydroxyphenyl)pyrazole-4-carboxamide 22 is obtained by purification of the crude product with HPLC.

Workup

  1. customafter reaction
  2. filtrationthe mixture is filtered through Celite
  3. washrinsed with ethyl acetate
  4. additionThe filtrate is diluted with ethyl acetate
  5. washis washed successively with aq. NaHCO3 and with half-saturated brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give the crude product

Sources & evidence

ORD record
ord-0c8348c681f14e51b0d1e625f6c745cc
Source dataset
uspto-grants-2004_06
Patent number
US06750241B2

Reaction notes

Loading…