Hydroxyphenylacetic acid → HCID 66907194, compound

HRID 1690485Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][CH:26]=1>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:29][CH:30]=1

Participants

Reactant 2

HCID 127Hydroxyphenylacetic acid

HCID 86634410HCID 86634410, compound

Product 1

HCID 66907194HCID 66907194, compoundYield 74%

Procedure

Using an analogous procedure to that described in the portion of Note [1] above that is concerned with the preparation of starting materials, 4-chloro-6-methoxy-7-(2-tetrahydropyran-2-yloxyethoxy) quinazoline was reacted with 2-(4-hydroxyphenyl)acetic acid to give 2-{4-[6-methoxy-7-(2-tetrahydropyran-2-yloxyethoxy)quinazolin-4-yloxy]phenyl}acetic acid in 74% yield; 1H NMR: (DMSOd6) 1.5 (m, 4H), 1.7 (m, 2H), 3.45 (m, 1H), 3.6 (s, 2H), 3.8 (m, 2H), 3.95 (s, 3H), 4.0 (m, 1H), 4.35 (m, 2H), 4.7 (s, 1H), 7.25 (d, 2H), 7.35 (d, 2H), 7.4 (s, 1H), 7.55 (s, 1H), 8.55 (s, 1H); Mass Spectrum: M+H+ 455.

Sources & evidence

ORD record: ord-3ed88592966247e28cc42f2854017f98
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153643B2

Reaction notes

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