HCID 118036390, compound → HCID 118036736, compound

HRID 1777873Notes

Reaction equation

HRID 1777873 reaction equation
[C:1]([C:3]1[C:4]([C:27]2[CH2:28][CH2:29][O:30][CH2:31][CH:32]=2)=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH:22]([O:25][CH3:26])[O:23][CH3:24])[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2]>CO.C1COCC1.[Pd]>[C:1]([C:3]1[C:4]([CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH:22]([O:25][CH3:26])[O:23][CH3:24])[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2]

Participants

5

Reactant 1

HCID 118036390HCID 118036390, compound2×

Product 1

HCID 118036736HCID 118036736, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(5-cyano-4-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 27, 35 mg, 0.080 mmol) was dissolved in MeOH (1 ml) and THF (3 ml). The solution was treated with palladium (10% on charcoal, 8.55 mg, 8.04 μmol) and stirred under a H2 atmosphere at room temperature for 16 h. The reaction mixture was filtered through a celite plug. The plug was rinsed with EtOAc and the filtrate was concentrated under vacuum. The residue was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a white solid. (UPLC-MS 3) tR 1.18 min; ESI-MS 438.2 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a celite plug
  2. washThe plug was rinsed with EtOAc
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100)

Sources & evidence

ORD record
ord-60ff049efa0c4c81888be82e0a0e5d30
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

Loading…