Potassium Carbonate → N-[4-(7-Benzyloxy-6-methoxy-quinazolin-4-yloxy)-phenyl]-benzamide

HRID 1686005Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[OH:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:31][CH:30]=1>CC(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:43])[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:31][CH:30]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 7-benzyloxy-4-chloro-6-methoxy-quinazoline (100 mg, 0.333 mmol), K2CO3 (345 mg, 2.49 mmol) and N-(4-hydroxy-phenyl)-benzamide (106 mg, 0.499 mmol) in DMA was heated at 50° C. for 18 hours. The reaction was cooled and partitioned between ice water and EtOAc. The aqueous was extracted twice with EtOAc and the combine organic washed with water, brine, dried and concentrated. The residue was purified by column chromatography (30-100% EtOAc:Heptane) to provide the title compound as a cream solid (120 mg).

Workup

temperatureThe reaction was cooled
custompartitioned between ice water and EtOAc
extractionThe aqueous was extracted twice with EtOAc
washthe combine organic washed with water, brine
customdried
concentrationconcentrated
customThe residue was purified by column chromatography (30-100% EtOAc:Heptane)

Sources & evidence

ORD record: ord-c3d8c9a8b418432985243ca9288902d8
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148531B2

Reaction notes

Loading…