HCID 54680316, compound → HCID 57882340, compound

HRID 1817356Notes

Reaction equation

HRID 1817356 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:25])[C:10](=[O:24])[N:11]([CH:21]([CH3:23])[CH3:22])[C:12]=2[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:7]1=[O:26].[H][H]>[Pd].CO>[F:30][C:29]1[CH:28]=[CH:27][C:4]([CH2:5][N:6]2[CH2:15][CH2:14][C:13]3[C:8](=[C:9]([OH:25])[C:10](=[O:24])[N:11]([CH:21]([CH3:22])[CH3:23])[C:12]=3[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:7]2=[O:26])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 54680316HCID 54680316, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57882340HCID 57882340, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-N,N-dimethyl-2-isopropyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (95 mg, 0.22 mmol; Example 13) and 10% palladium on charcoal (0.11 g) in methanol (5 mL) was stirred under a balloon of hydrogen gas at room temperature overnight. The reaction mixture was filtered, and the filtrate concentrated under vacuum. The residue was subjected to preparative HPLC purification on C-18 reverse stationary phase column eluting with a gradient of water—acetonitrile in the presence of 0.1% trifluoroacetic acid. Collection and lyophilization of appropriate fractions provided the titled compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe residue was subjected to preparative HPLC purification on C-18 reverse stationary phase column
  4. washeluting with a gradient of water—acetonitrile in the presence of 0.1% trifluoroacetic acid
  5. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-d36d3fdca8424ccd83c47fb26556c790
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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