(+-)-Methionine → HCID 178480343, compound

HRID 640020Notes

Reaction equation

HRID 640020 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12]C)[CH:10]=2)[N:5]=[CH:4][N:3]=1.NC(C(O)=[O:30])CCSC.[OH-].[Na+]>CS(O)(=O)=O>[CH3:22][N:19]1[CH2:20][CH2:21][CH:16]([CH2:15][O:14][C:8]2[CH:7]=[C:6]3[C:11]([C:2]([OH:30])=[N:3][CH:4]=[N:5]3)=[CH:10][C:9]=2[OH:12])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 876(+-)-MethionineHCID 14798Sodium HydroxideHCID 117822304-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline

Product 1

HCID 178480343HCID 178480343, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline (see Journal of Medicinal Chemistry, 2002, 45, 1300-12, 9.8 g, 30 mmol), D,L-methionine (7.15 g, 48 mmol) and methanesulphonic acid (50 ml) was heated at 150° C. for 32 hours. The reaction mixture was allowed to cool to room temperature. The pH was adjusted to 8 with aqueous sodium hydroxide then, aqueous sodium hydrogen carbonate and concentrated to half the original volume. The resultant solid was filtered and washed with water and then dried for 16 hours at 60° C. to give 7-[(1-methylpiperidin-4-yl)methoxy]quinazoline-4,6-diol (6.16 g, 71% yield).

Workup

  1. temperatureto cool to room temperature
  2. concentrationaqueous sodium hydrogen carbonate and concentrated to half the original volume
  3. filtrationThe resultant solid was filtered
  4. washwashed with water
  5. customdried for 16 hours at 60° C.

Sources & evidence

ORD record
ord-e569a473852b4525888d54b188b54b45
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

Loading…