Dichloromethane → HCID 59603032, compound

HRID 1951423Notes

Reaction equation

HRID 1951423 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH:11]1[C:20]2[C:19](=[O:21])[NH:18][CH:17]=[CH:16][C:15]=2[NH:14][C:13]([CH3:22])=[C:12]1[N+:23]([O-:25])=[O:24])[C:6]#[N:7].F[B-](F)(F)F.[CH2:31]([O+](CC)CC)[CH3:32].ClCCl>CO>[CH2:31]([O:21][C:19]1[N:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[CH:11]([C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:2][CH3:1])[C:12]([N+:23]([O-:25])=[O:24])=[C:13]([CH3:22])[NH:14]2)[CH3:32]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2723982Triethyloxonium tetrafluoroborateHCID 59603027HCID 59603027, compound

Product 1

HCID 59603032HCID 59603032, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40 mg (0.11 mmol) of 3-methoxy-4-(2-methyl-3-nitro-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)benzonitrile and 43 mg of triethyloxonium tetrafluoroborate (0.23 mmol) are mixed under a dry argon atmosphere. After addition of dichloromethane (5 ml), the suspension is stirred until a solution is obtained, then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 13 mg (29% of theory) of the title compound as a white solid.

Workup

  1. customis obtained
  2. concentrationconcentrated
  3. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-6fd21afbba0e4e08b6c5aca7b1e9123b
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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