Ammonium formate → HCID 118699713, compound

HRID 1773317Notes

Reaction equation

HRID 1773317 reaction equation
Cl[C:2]1[C:11]2[CH2:10][NH:9][CH2:8][CH2:7][C:6]=2[C:5]2[S:12][CH:13]=[CH:14][C:4]=2[N:3]=1.C([O-])=O.[NH4+]>CCO.[Pd]>[S:12]1[C:5]2[C:6]3[CH2:7][CH2:8][NH:9][CH2:10][C:11]=3[CH:2]=[N:3][C:4]=2[CH:14]=[CH:13]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 118699730HCID 118699730, compound

Product 1

HCID 118699713HCID 118699713, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-Chloro-6,7,8,9-tetrahydrothieno[3,2-c]-2,7-naphthyridine (3.22 g, 14.33 mmol), 10% Pd on C (500 mg) and ammonium formate (8.13 g, 128.97 mmol) in EtOH (125 ml) was heated at 80° C. for 24 hours. Analytical data (TLC, MS) confirmed complete removal of chlorine to give both the title compound along with the N-formyl analog. Upon cooling, the catalyst was filtered off (celite) and the filtrate was treated with NaOH(aq.) until pH ˜14. The alkaline reaction mixture was refluxed for 33 hours, cooled, filtered and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 9:1 EtOAc:7M NH3 in MeOH) gave the title compound as a viscous yellow oil which crystallized on standing (1.96 g, 72%).

Workup

  1. customremoval of chlorine

Sources & evidence

ORD record
ord-d9ce88ed12d340bc81cbaded0bb3402f
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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