2-Methoxyphenylboronic acid → HCID 135873929, compound

HRID 1428901Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:20](COCC[Si](C)(C)C)[C:19](=[O:29])[C:18]3[C:13](=[CH:14][CH:15]=[C:16](I)[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O>>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([N:9]1[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]1)[NH:20][C:19]2=[O:29]

Participants

Reactant 2

HCID 27339582-Methoxyphenylboronic acid

HCID 68487682HCID 68487682, compound

Product 1

HCID 135873929HCID 135873929, compound

Procedure

The titled compound was prepared in a manner analogous to Example 69, steps C-E, using 1-[6-iodo-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (Example 69 product from step B) and 2-methoxyphenylboronic acid in step C. MS (ESI): mass calcd. for C19H14N4O4, 362.1; m/z found, 363.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.00 (br s, 1H), 12.84 (br s, 1H), 8.98 (s, 1H), 8.28 (s, 1H), 8.21 (d, J=1.7 Hz, 1H), 7.97 (dd, J=8.4, 2.1 Hz, 1H), 7.74 (d, J=7.0 Hz, 1H), 7.43-7.39 (m, 2H), 7.19-7.16 (m, 1H), 7.09 (td, J=7.5, 1.0 Hz, 1H), 3.81 (s, 3H).

Sources & evidence

ORD record: ord-cf46e85741bc46eaaf8d7370a5caa8d7
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937078B2

Reaction notes

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