(3-Methoxyphenyl)boronic acid → HCID 136027644, compound

HRID 1428902Notes

Reaction equation

HRID 1428902 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:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1>>[CH3:31][O:32][C:33]1[CH:38]=[C:37]([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([N:9]2[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]2)[NH:20][C:19]3=[O:29])[CH:36]=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 68487682HCID 68487682, compound

Product 1

HCID 136027644HCID 136027644, 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 3-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): 13.01 (br s, 1H), 12.91 (br s, 1H), 8.98 (s, 1H), 8.34 (s, 1H), 8.28 (s, 1H), 8.18 (d, J=6.7 Hz, 1H), 7.78 (s, 1H), 7.44 (t, J=7.9 Hz, 1H), 7.35 (d, J=7.8 Hz, 1H), 7.29 (s, 1H), 7.00 (dd, J=8.2, 1.8 Hz, 1H), 3.86 (s, 3H).

Sources & evidence

ORD record
ord-b4e875ab47cf434fb74112dbce5aff1d
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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