Ammonium formate → HCID 117667759, compound

HRID 712641Notes

Reaction equation

HRID 712641 reaction equation
[O:1]=[S:2]1(=[O:27])[CH2:7][CH:6]=[C:5]([C:8]2[CH:9]=[C:10]([C:14]3[CH:15]=[C:16]4[C:21](=[N:22][CH:23]=3)[N:20]([C:24]([NH2:26])=[O:25])[CH2:19][CH2:18][CH2:17]4)[CH:11]=[N:12][CH:13]=2)[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>[Pd].CO>[O:27]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[C:10]([C:14]3[CH:15]=[C:16]4[C:21](=[N:22][CH:23]=3)[N:20]([C:24]([NH2:26])=[O:25])[CH2:19][CH2:18][CH2:17]4)[CH:11]=[N:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 117667332HCID 117667332, compound

Product 1

HCID 117667759HCID 117667759, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To the mixture of 6-[5-(1,1-dioxo-1,2,3,6-tetrahydro-1lambda6-thiopyran-4-yl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (56 mg, 0.15 mmol) and 10% Pd/C (17 mg) is added 2 mL of MeOH under Ar. Then ammonium formate (140 mg, 2.20 mmol) is added and the mixture is stirred for 1 hr at 80° C. The mixture is filtered, concentrated and purified via Preparative HPLC (10%-80% CH3CN/H2O) to give 30.2 mg of the titled product.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated
  3. custompurified via Preparative HPLC (10%-80% CH3CN/H2O)

Sources & evidence

ORD record
ord-9072fe4d0a054b7f9a42e21c86f5735e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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