Ethyl Acetate → HCID 12150417, compound

HRID 392171Notes

Reaction equation

HRID 392171 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-52a2f81ff50f4b4ea5a3f5821f385092
Source dataset
uspto-grants-2004_10
Patent number
US06800644B2

Reaction notes

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