Pyridine → HCID 69060904, compound

HRID 1817351Notes

Reaction equation

HRID 1817351 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:22][CH3:23])[C:10](=[O:21])[NH:11][C:12]=2[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:7]1=[O:24].B(O)(O)[C:30]1[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=1.N1C=CC=CC=1.[NH4+].[OH-]>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:22][CH3:23])[C:10](=[O:21])[N:11]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)[C:12]=2[C:16]([N:18]([CH3:19])[CH3:20])=[O:17])[C:7]1=[O:24]

Participants

8

Reactant 4

HCID 1049PyridineHCID 14923Ammonium HydroxideHCID 79799Tolylboronic acidHCID 69064860HCID 69064860, compound

Product 1

HCID 69060904HCID 69060904, compound

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(3-chloro-4-fluorobenzyl)-4-methoxy-N,N-dimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (0.10 g, 0.25 mmol), p-tolylboronic acid (0.13 g, 0.98 mmol), copper (II) acetate (67 mg, 0.37 mmol), activated molecular sieves type 4A (1 g), and pyridine (40 mg, 0.50 mmol) in dichloromethane (12 mL) was stirred at room temperature overnight. The reaction mixture was treated with a mixture of aqueous NH4OH (1 mL, 1M) and methanol (3 mL). After stirring at room temperature for 15 minutes, the slurry was filtered, and the filtrate concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a gradient of 0 to 15% of methanol in chloroform. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. stirringAfter stirring at room temperature for 15 minutes
  2. filtrationthe slurry was filtered
  3. concentrationthe filtrate concentrated under vacuum
  4. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-10e8773051ac429e8bed4bea521f3b7a
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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