Cesium acetate → Desmethyl Erlotinib Acetate

HRID 1869086Notes

Reaction equation

HRID 1869086 reaction equation
Cl.Cl[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][N:10]=[C:9]2[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[CH:29])[CH:23]=1.[C:30]([O-:33])(=[O:32])[CH3:31].[Cs+]>CN(C=O)C>[C:30]([O:33][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][N:10]=[C:9]2[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[CH:29])[CH:23]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 5152919Cesium acetateHCID 189250626-O-Desmethoxyethyl-6-O-chloroethyl Erlotinib Hydrochloride

Product 1

HCID 16045727Desmethyl Erlotinib AcetateYield 183.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title product of Example 30 (160 mg, 0.368 mmol); was treated with cesium acetate (707 mg, 3.68 mmol) in DMF (3 mL) at 120° C. under an atmosphere of N2 for 16 hours. The reaction mixture was partitioned between brine and CHCl3, and the organic extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford a residue (285 mg) which was recrystallized from ethylacetate/hexane. (134 mg; M.P. 84°-87° C.; LC-MS: 422 (MH+); anal. RP18-HPLC RT: 4.38 min.).

Workup

  1. customThe reaction mixture was partitioned between brine and CHCl3
  2. extractionthe organic extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9447e2b0b7564efdbda24369bf4e7cd1
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Reaction notes

Loading…