Dimethylmethylenammonium chloride → 2-Dimethylaminomethyl-9-hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one hydrochloride

HRID 1776160Notes

Reaction equation

HRID 1776160 reaction equation
[OH:1][C:2]1[C:3]2[C:4]3[N:15]=[CH:14][S:13][C:5]=3[NH:6][C:7](=[O:12])[C:8]=2[CH:9]=[CH:10][CH:11]=1.[Cl-:16].[CH3:17][N+:18]([CH3:20])=[CH2:19]>CN(C=O)C.C(#N)C>[ClH:16].[CH3:17][N:18]([CH2:20][C:14]1[S:13][C:5]2[NH:6][C:7](=[O:12])[C:8]3[CH:9]=[CH:10][CH:11]=[C:2]([OH:1])[C:3]=3[C:4]=2[N:15]=1)[CH3:19]

Participants

4

Reactant 2

HCID 11051579Dimethylmethylenammonium chlorideHCID 580160609-Hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one

Product 1

HCID 670764312-Dimethylaminomethyl-9-hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one hydrochlorideYield 13%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

To a solution of 9-hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one in DMF/acetonitrile (3 ml, 1:2) was added dimethyl-methylene-ammonium chloride (0.043 g, 0.46 mmol) and the resulting mixture was refluxed under Ar for 42 hours. After cooling and concentration, the residue was purified via flash chromatography on SiO2 to give the title compound (0.008 g, a 13% yield) as solid. m.p.>250° C.; 1H NMR (400 MHz, DMSO) δ 2.36 (s, 6H, N(CH3)2), 3.93 (m, 2H, CH2N), 7.24 (d, 1H, Ar), 7.44 (t, 1H, Ar), 7.74 (d, 1H, Ar), 10.23 (s, 1H, OH), 12.30 (s, 1H, NH); 13C NMR (100.6 MHz, DMSO) δ 46.83, 61.38, 119.94, 120.56, 121.00, 126.83, 129.95, 131.75, 137.39, 154.41, 162.54.

Workup

  1. temperaturethe resulting mixture was refluxed under Ar for 42 hours
  2. temperatureAfter cooling
  3. concentrationconcentration
  4. customthe residue was purified via flash chromatography on SiO2

Sources & evidence

ORD record
ord-8bade023557c4cb8836ecb87955760a5
Source dataset
uspto-grants-2016_02
Patent number
US09265769B2

Reaction notes

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