Potassium Carbonate → 2-[7-(3-Fluoro-benzyloxy)-2-methyl-4-oxo-4H-quinazolin-3-yl]-acetamide

HRID 7628

Reaction equation

FC1C=C(C=CC=1)CO[C:7](=[O:26])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[CH:10][C:9]=1[N+:23]([O-])=O.COC(=O)[C:33]1C=CC(OCC2C=CC=C(F)C=2)=C[C:34]=1[N+:48]([O-])=O.COC(=O)C1C=CC(F)=[CH:57][C:56]=1[N+:62]([O-])=O.FC1C=C(C=CC=1)C[OH:71].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:11]1[CH:10]=[C:9]2[C:8]([C:7](=[O:26])[N:48]([CH2:57][C:56]([NH2:62])=[O:71])[C:34]([CH3:33])=[N:23]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 65 °C

Procedure

4-(3-Fluoro-benzyloxy)-2-nitro-benzoic acid (3-fluoro-benzyl) ester and 4-(3-fluoro-benzyloxy)-2-nitro-benzoic acid methyl ester: A mixture of 4-fluoro-2-nitro-benzoic acid methyl ester (9.2 g, 46.3 mmol), 3-fluorobenzyl alcohol (16.7 g, 132.4 mmol) and potassium carbonate (12.8 g, 92.6 mmol) in DMF (210 mL) was heated at 65° C. for 48 h. After cooling to rt, the mixture was poured into water (400 mL), and extracted with diethyl ether (3×100 mL). The combined extracts were washed with brine (100 mL) dried and evaporated. Purification by chromatography on silica gel eluting with ethyl acetate:hexane (1:1) afforded the title compound (14.0 g, 76%) as a light yellow liquid.

Workup

temperatureAfter cooling to rt
extractionextracted with diethyl ether (3×100 mL)
washThe combined extracts were washed with brine (100 mL)
customdried
customevaporated
customPurification by chromatography on silica gel eluting with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record: ord-f243056d574b4911b9c3d4786237c32f
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087612B2

Linked notes

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