Ammonium formate → HCID 16679576, compound

HRID 2265413Notes

Reaction equation

HRID 2265413 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-17308737a72d4a5fafb00b78716c809b
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

Loading…