Ammonium formate → HCID 16679576, compound

HRID 218644Notes

Reaction equation

HRID 218644 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:36]1[CH:41]=[CH:40][C:39]([CH:42]([CH3:44])[CH3:43])=[CH:38][CH:37]=1)[CH2:22][C:23]1[CH:24]=[N:25][C:26]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:27][CH:28]=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:36]1[CH:41]=[CH:40][C:39]([CH:42]([CH3:44])[CH3:43])=[CH:38][CH:37]=1)[CH2:22][C:23]1[CH:24]=[N:25][C:26]([O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:27][CH:28]=1)=[O:20]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59597353HCID 59597353, compound

Product 1

HCID 16679576HCID 16679576, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-benzyloxy-N-(4-isopropylphenyl)-N-[(6-phenoxypyridin-3-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.42 g) in methanol (3 mL) were added 10% palladium carbon (0.05 g) and ammonium formate (0.23 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-[(6-phenoxypyridin-3-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide. This compound was dissolved in ethyl acetate, and 4 mol/L-hydrochloric acid/dioxane (0.20 mL) was added. The precipitated solid was collected by filtration to give 5-hydroxy-N-(4-isopropylphenyl)-N-[(6-phenoxypyridin-3-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide hydrochloride (0.11 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-e439d3dc38274db5a32d06ea5d78dd74
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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