Hydrochloric Acid → 4-(5-Aminomethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

HRID 1690741ノート

反応式

HRID 1690741 の反応式
[CH3:1][C:2]1([CH3:20])[CH:11]([N:12]2[C:16]([C:17]#[N:18])=[CH:15][N:14]=[CH:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:19])[O:3]1.Cl.CO>C1COCC1>[NH2:18][CH2:17][C:16]1[N:12]([CH:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:19])[O:3][C:2]2([CH3:20])[CH3:1])[CH:13]=[N:14][CH:15]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24805168HCID 24805168、化合物

生成物 1

HCID 577811204-(5-Aminomethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The solution of 3-(3,3-dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbonitrile (0.130 g, 0.5 mmol) (Example 20) in THF (2 mL) is added borane dimethyl sulfide complex (0.055 mL, 0.55 mmol) dropwise, and the resulting mixture is stirred at reflux for 30 min. The reaction mixture is concentrated in vacuo and the residue is redissolved in THF (2 mL) and 0.5 M hydrogen chloride in methanol (1.1 mL, 0.55 mmol) is added dropwise. The reaction mixture is stirred at ambient temperature for 1.5 h. The mixture is concentrated in vacuo and the residue is purified by semi-preparative reverse phase HPLC to give 4-(5-aminomethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a yellowish solid; MS (ESI) m/z 271.9 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 1.28 (s, 3 H), 1.59 (s, 3 H), 4.55-4.74 (m, 2 H), 5.99 (s, 1 H), 7.67-7.76 (m, 3 H), 7.82 (td, J=7.6, 1.5 Hz, 1 H), 8.29 (dd, J=7.7, 1.4 Hz, 1H), 8.52 (br. s, 1 H)

後処理

  1. temperatureat reflux for 30 min
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. dissolutionthe residue is redissolved in THF (2 mL)
  4. stirringThe reaction mixture is stirred at ambient temperature for 1.5 h
  5. concentrationThe mixture is concentrated in vacuo
  6. customthe residue is purified by semi-preparative reverse phase HPLC

出典と根拠

ORDレコード
ord-14049ed1fe6446a1a1a0e30fa59f62bc
出典データセット
uspto-grants-2012_04
特許番号
US08153674B2

反応ノート

読み込み中…