Ammonium formate → HCID 59597277, compound

HRID 2265416Notes

Reaction equation

HRID 2265416 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[C:19]([N:21]([C:34]1[CH:39]=[CH:38][C:37]([CH:40]([CH3:42])[CH3:41])=[CH:36][CH:35]=1)[CH2:22][C:23]1[CH:24]=[N:25][N:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:27]=1)=[O:20])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[C].[Pd]>[OH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[C:19]([N:21]([C:34]1[CH:39]=[CH:38][C:37]([CH:40]([CH3:42])[CH3:41])=[CH:36][CH:35]=1)[CH2:22][C:23]1[CH:24]=[N:25][N:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:27]=1)=[O:20]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59597216HCID 59597216, compound

Product 1

HCID 59597277HCID 59597277, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-benzyloxy-N-(4-isopropylphenyl)-N-[(1-phenylpyrazol-4-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide (1.04 g) in methanol (10 mL) were added 10% palladium carbon (0.10 g) and ammonium formate (0.59 g), and the mixture was stirred at room temperature for one day. The reaction mixture was filtrated, and the solvent was evaporated. The residue was purified by silica gel column chromatography to give 5-hydroxy-N-(4-isopropylphenyl)-N-[(1-phenylpyrazol-4-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.76 g).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3fe62597166b402b9ccb05d815e80ccb
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

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