HCID 60112841, compound → HCID 10115992, compound

HRID 445169Notes

Reaction equation

HRID 445169 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][C:22]#[CH:23])[CH:18]=3)[N:13]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][O:34]C4CCCCO4)[CH:26]=3)[C:12](=[O:41])[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>CO>[OH:34][CH2:33][CH2:32][O:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][N:13]1[C:14]2[C:19](=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[CH:16][CH:15]=2)[C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][CH:8]=2)=[N:11][C:12]1=[O:41]

Participants

3

Reactant 1

HCID 60112841HCID 60112841, compound

Product 1

HCID 10115992HCID 10115992, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 76 mg (0.14 mmol) of 4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1-{3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzyl}-1H-quinazolin-2-one (Example RT-6) in MeOH (10 ml) is added 10 wt % Dowex-50 and the mixture is stirred vigorously for 3 days. The reaction mixture is filtered and the solvent is removed in vacuo. The residue is dissolved in CH2Cl2 and extracted with water and then brine, dried (MgSO4), filtered and evaporated in vacuo to provide a yellow oil which is purified by preparative TLC of silica gel using dichloromethane/ether (1:1) to provide the title compound as a yellow oil. Yield: 11 mg (17%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe solvent is removed in vacuo
  3. dissolutionThe residue is dissolved in CH2Cl2
  4. extractionextracted with water
  5. dry with materialbrine, dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto provide a yellow oil which
  9. customis purified by preparative TLC of silica gel

Sources & evidence

ORD record
ord-1d0548015e2c4ed0ab4b9a5aae2460f3
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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