Ammonium formate → HCID 135788276, compound

HRID 1822742Notes

Reaction equation

HRID 1822742 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-1f9c094a76aa473db1d33e2d54b696c8
Source dataset
uspto-grants-2006_05
Patent number
US07037912B2

Reaction notes

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