(3-Phenylphenyl)boronic acid → HCID 135895254, compound

HRID 1428831Notes

Reaction equation

HRID 1428831 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.[C:31]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:36]=[CH:35][CH:34]=[C:33](B(O)O)[CH:32]=1>>[C:31]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:36]=[CH:35][CH:34]=[C:33]([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:32]=1

Participants

3

Reactant 2

HCID 2734315(3-Phenylphenyl)boronic acidHCID 68487682HCID 68487682, compound

Product 1

HCID 135895254HCID 135895254, 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 (product from Example 69, step B) and biphenyl-3-boronic acid. MS (ESI): mass calcd. for C24H16N4O3, 408.1; m/z found, 409.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.01 (s, 1H), 12.92 (s, 1H), 9.00 (s, 1H), 8.44 (s, 1H), 8.32-8.25 (m, 2H), 8.01 (s, 1H), 7.83-7.77 (m, 4H), 7.72 (d, J=7.8 Hz, 1H), 7.62 (t, J=7.7 Hz, 1H), 7.53-7.48 (m, 2H), 7.43-7.40 (m, 1H).

Sources & evidence

ORD record
ord-6cc662b2f1b54b92a2c60f5893d2ce00
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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