Ammonium formate → HCID 117667206, compound

HRID 712661Notes

Reaction equation

HRID 712661 reaction equation
[C:1]([N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[N:24][CH:25]=3)[N:22]([C:26]([NH2:28])=[O:27])[CH2:21][CH2:20][CH2:19]4)[CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[N:24][CH:25]=3)[N:22]([C:26]([NH2:28])=[O:27])[CH2:21][CH2:20][CH2:19]4)[CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 117667539HCID 117667539, compound

Product 1

HCID 117667206HCID 117667206, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-(1′-acetyl-1′,2′,3′,6′-tetrahydro-[3,4]bipyridinyl-5-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (91 mg, 0.24 mmol) in 2.0 mL of MeOH is added 10% Pd/C (38 mg, 0.036 mmol). Then ammonium formate (60 mg, 0.96 mmol) is added and the mixture is stirred for 2 hrs at 80° C. The solid of the reaction mixture is filtered and the filtrate is concentrated to give the crude product. Purification by flash column chromatography affords 38 mg of 6-(1′-acetyl-1′,2′,3′,4′,5′,6′-hexahydro-[3,4]bipyridinyl-5-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide.

Workup

  1. filtrationThe solid of the reaction mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customto give the crude product
  4. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-96397f120cb14359a713731d4446cfac
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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