Methanol → 4-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-3-ethylbenzonitrile

HRID 1951414Notes

Reaction equation

HRID 1951414 reaction equation
[C:1]([C:4]1[CH:13]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=2[CH2:22][CH3:23])[C:12]2[C:11](=[O:24])[NH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:5]=1[CH3:25])(=[O:3])[CH3:2].F[B-](F)(F)F.[CH2:31]([O+](CC)CC)[CH3:32].CO>ClCCl>[C:1]([C:4]1[CH:13]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=2[CH2:22][CH3:23])[C:12]2[C:7](=[CH:8][CH:9]=[N:10][C:11]=2[O:24][CH2:31][CH3:32])[NH:6][C:5]=1[CH3:25])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 2723982Triethyloxonium tetrafluoroborateHCID 596030194-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-ethylbenzonitrile

Product 1

HCID 596030184-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-3-ethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

275 mg (0.82 mmol) of 4-(3-acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-ethylbenzonitrile are suspended under an argon atmosphere in dichloromethane (10 ml), 313 mg (1.65 mmol) of triethyloxonium tetrafluoroborate are added, and the mixture is stirred at RT for 12 h. The reaction mixture is then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 152 mg (50% of theory) of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-d60b9e44d1be47af865943282a68a44c
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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