Dichloromethane → HCID 67416799, compound

HRID 1951422Notes

Reaction equation

HRID 1951422 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[NH:16][CH:15]=[CH:14][C:13]=3[NH:12][C:11]([C:20]([F:23])([F:22])[F:21])=[C:10]2[C:24]#[N:25])=[C:5]([O:26][CH3:27])[CH:4]=1)#[N:2].F[B-](F)(F)F.[CH2:33]([O+](CC)CC)[CH3:34].ClCCl>CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[N:16][C:17]=3[O:19][CH2:33][CH3:34])[NH:12][C:11]([C:20]([F:23])([F:22])[F:21])=[C:10]2[C:24]#[N:25])=[C:5]([O:26][CH3:27])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2723982Triethyloxonium tetrafluoroborateHCID 67417398HCID 67417398, compound

Product 1

HCID 67416799HCID 67416799, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

390 mg (1.05 mmol) of 4-(4-cyano-2-methoxyphenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carbonitrile and 398 mg of triethyloxonium tetrafluoroborate (2.1 mmol) are mixed under a dry argon atmosphere. After addition of dichloromethane (32 ml), the suspension is stirred until a solution is obtained (about 2 h), and then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 250 mg (59% of theory) of the title compound as a white solid.

Workup

  1. customis obtained (about 2 h)
  2. concentrationconcentrated
  3. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-cde44cde1a394319881bbfcc4b4af56d
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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