Tolylboronic acid → HCID 136027559, compound

HRID 1428894Notes

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][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>>[O:29]=[C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:35]3[CH:36]=[CH:37][C:32]([CH3:31])=[CH:33][CH:34]=3)[CH:17]=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]1

Participants

Reactant 2

HCID 79799Tolylboronic acid

HCID 68487682HCID 68487682, compound

Product 1

HCID 136027559HCID 136027559, 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 4-methylphenylboronic acid in step C. MS (ESI): mass calcd. for C19H14N4O3, 346.1; m/z found, 347.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.03 (s, 1H), 12.92 (s, 1H), 8.98 (s, 1H), 8.33 (s, 1H), 8.27 (s, 1H), 8.16 (d, J=7.9 Hz, 1H), 7.77 (s, 1H), 7.69 (d, J=8.0 Hz, 2H), 7.33 (d, J=7.9 Hz, 2H), 2.37 (s, 3H).

Sources & evidence

ORD record: ord-7264af7fc9584e6c9d12f005eac6f13b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937078B2

Reaction notes

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