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

HRID 1690741노트

반응식

HRID 1690741 반응식
[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

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24805168HCID 24805168, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-14049ed1fe6446a1a1a0e30fa59f62bc
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153674B2

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