Ethyl Acetate → HCID 12150417, compound

HRID 275736Notes

Reaction equation

HRID 275736 reaction equation
C([O:8][C:9]1[CH:39]=[CH:38][C:12]([C:13]([NH:15][C:16]2[CH:17]=[C:18]([C:22]3[C:31]4[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=4)[N:25]=[C:24]([NH:36][CH3:37])[N:23]=3)[CH:19]=[CH:20][CH:21]=2)=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1.C(OCC)(=O)C.[H][H]>[C].[Pd].O1CCCC1>[CH3:33][O:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH3:35])[N:25]=[C:24]([NH:36][CH3:37])[N:23]=[C:22]2[C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:39][CH:38]=2)[CH:17]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 12150416HCID 12150416, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12150417HCID 12150417, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

388 mg of 4-[3-(4-benzyloxybenzoylamino)phenyl]-6,7-dimethoxy-2-methylaminoquinazoline obtained in Example 20 and 200 mg of 10% palladium-carbon powder (hydrate) were suspended in a mixed solvent of 10 ml ethyl acetate and 10 ml tetrahydrofuran. After the atmosphere was replaced with hydrogen, the mixture was stirred for 3 days at ordinary pressure at room temperature. The reaction solution was filtered, and the filtrate was evaporated. Then, the crude product was recrystallized from hexane-ethyl acetate to give 278 mg of the title compound as pale yellow crystals.

Workup

  1. filtrationThe reaction solution was filtered
  2. customthe filtrate was evaporated
  3. customThen, the crude product was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-51a3dc2a8a3e4768b74707d4d99aeed9
Source dataset
uspto-grants-2002_03
Patent number
US06352989B1

Reaction notes

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