HCID 18762004, compound → HCID 69905062, compound

HRID 430903Notes

Reaction equation

HRID 430903 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[CH:8]=[C:9]([C:13]#[C:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)[CH:10]=[N:11][CH:12]=1>CO>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[CH:12]=[N:11][CH:10]=[C:9]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=2)[CH:8]=1

Participants

3

Reactant 1

HCID 18762004HCID 18762004, compound

Product 1

HCID 69905062HCID 69905062, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of YH19 (0.15 g, 0.468 mmol) and Pd(C) (10%, 20 mg) in MeOH (10 mL) was hydrogenated at atmospheric pressure and room temperature for one day. The catalyst was removed by filtration through Celite and the filtrate was concentrated. The residue was chromatographed [SiO2, CHCl3/MeOH (60:1)] to give 0.15 g (95%) of YH22; 1H NMR (400 MHz, CDCl3) δ 8.38 (br s, 2H), 7.91-7.80 (m, 2H), 7.40 (s, 1H), 7.16-7.14 (m, 2H), 3.85 (s, 3H), 3.23-3.16 (m, 1H), 3.05-2.87 (m, 5H), 2.30-2.22 (m, 1H), 2.18-2.08 (m, 1H), 2.09 (s, 3H), 1.92-1.84 (m, 1H), 1.81-1.72 (m, 1H), 1.67-1.57 (m, 1H); 13C NMR (400 MHz, CDCl3) δ 166.9, 148.6, 147.3, 146.2, 138.3, 136.5, 134.5, 129.7, 128.0, 68.6, 56.9, 51.9, 40.2, 37.4, 35.0, 34.4, 22.4;

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was chromatographed [SiO2, CHCl3/MeOH (60:1)]
  4. customto give 0.15 g (95%) of YH22

Sources & evidence

ORD record
ord-30ee736460c943088a8e7d2681e63854
Source dataset
uspto-grants-2003_12
Patent number
US06656469B1

Reaction notes

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