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

HRID 1776160ノート

反応式

HRID 1776160 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21891449acetonitrile N,N-dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8bade023557c4cb8836ecb87955760a5
出典データセット
uspto-grants-2016_02
特許番号
US09265769B2

反応ノート

読み込み中…