2,4-Dimethoxybenzylamine → HCID 178491072, compound

HRID 2173054Notes

Reaction equation

HRID 2173054 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][NH2:12].[Cl:13][C:14]1[C:19]2[C:20](=[O:24])[O:21][CH:22](O)[C:18]=2[C:17]([F:25])=[C:16]([Cl:26])[N:15]=1>CO>[Cl:13][C:14]1[N:15]=[C:16]([Cl:26])[C:17]([F:25])=[C:18](/[CH:22]=[N:12]/[CH2:11][C:4]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=2[O:2][CH3:1])[C:19]=1[C:20]([OH:24])=[O:21]

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 58317608HCID 58317608, compound

Product 1

HCID 178491072HCID 178491072, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2,4-dimethoxyphenyl)methanamine (40.5 g, 242.0 mmol) in MeOH (250 mL) was added 4,6-dichloro-7-fluoro-1-hydroxyfuro[3,4-c]pyridin-3(1H)-one (55.0 g, 231.0 mmol). The mixture was stirred for 0.5 h, filtered, and washed with petroleum ether to give the title compound as a white solid (73.0 g, 82%). 1H NMR (CDCl3, 400 MHz) δ ppm 3.75 (s, 3H), 3.79 (s, 3H), 3.93 (s, 2H), 6.30 (s, 1H), 6.40-6.42 (m, 2H), 7.12 (d, J=8.4 Hz, 1H). [M+H] calc'd for C16H13Cl2FN2O4, 387. found, 387.

Workup

  1. filtrationfiltered
  2. washwashed with petroleum ether

Sources & evidence

ORD record
ord-2559b60bced0434f98b49640710c6dc9
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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