Ammonium formate → HCID 117667610, compound

HRID 712743Notes

Reaction equation

HRID 712743 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:22]3[CH:23]=[N:24][C:25]4[N:26]([C:32](=[O:34])[NH2:33])[CH2:27][CH2:28][CH2:29][C:30]=4[CH:31]=3)[C:19]=2[C:20]#[N:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:22]3[CH:23]=[N:24][C:25]4[N:26]([C:32](=[O:34])[NH2:33])[CH2:27][CH2:28][CH2:29][C:30]=4[CH:31]=3)[C:19]=2[C:20]#[N:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 117667569HCID 117667569, compound

Product 1

HCID 117667610HCID 117667610, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

5-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-4-cyano-3′,6′-dihydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (100 mg, 0.22 mmol), 10% Pd on carbon (88 mg, 0.083 mmol) and ammonium formate (210 mg, 3.3 mmol) are mixed in MeOH (2.0 mL). The reaction mixture is heated at 60° C. for 24 hrs. Then the solid is filtered and the filtrate is concentrated to give the crude 5-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-4-cyano-3′,4′,5′,6′-tetrahydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester which is used in the next step without purification.

Workup

  1. filtrationThen the solid is filtered
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-294a01a94cf9405eb86c0aae0ef7dd00
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…