Methylamine → HCID 17965954, compound

HRID 1348894Notes

Reaction equation

HRID 1348894 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:15](=[CH:21]O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][C:10](OCC)=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH3:23][NH2:24].C1COCC1.C([O-])([O-])=O.[K+].[K+]>C(O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][N:24]([CH3:23])[C:10](=[O:11])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 131726362HCID 131726362, compound

Product 1

HCID 17965954HCID 17965954, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of Example 41B (1.50 g, 4.62 mmol), 2M methylamine in THF (3.5 mL, 7.0 mmol), and acetic acid (1.5 mL) in ethanol (20 mL) was heated to reflux for 30 minutes, cooled to room temperature, and concentrated. The concentrate was dissolved in acetonitrile (15 mL), treated with K2CO3 (3.2 g, 23.0 mmol), stirred for 18 hours, and concentrated. The concentrate was dissolved in dichloromethane, washed with water, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 19:1 dichloromethane/acetone to provide 586 mg (41%) of the desired product. MS (DCI/NH3) m/z 292 (M+H)+; 1H NMR (CDCl3) δ 8.22 (s, 1H), 7.35 (m, 2H), 7.23 (m, 1H), 7.12 (m, 1H), 6.43 (s, 1H), 4.09 (q, 2H), 3.65 (s, 3H), 1.04 (t, 3H).

Workup

  1. temperatureto reflux for 30 minutes
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in acetonitrile (15 mL)
  4. concentrationconcentrated
  5. dissolutionThe concentrate was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate was purified by flash column chromatography on silica gel with 19:1 dichloromethane/acetone

Sources & evidence

ORD record
ord-acb24128a716420ca7545b98c0797852
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

Loading…