2-Ethylphenylboronic Acid (contains varying amounts of Anhydride) → HCID 136027588, compound

HRID 1428906Notes

Reaction equation

HRID 1428906 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.[CH2:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O)[CH3:32]>>[CH2:31]([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])[CH3:32]

Participants

3

Reactant 2

HCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 68487682HCID 68487682, compound

Product 1

HCID 136027588HCID 136027588, 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-ethylphenylboronic acid in step C. MS (ESI): mass calcd. for C20H16N4O3, 360.1; m/z found, 361.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.01 (br s, 1H), 12.91 (br s, 1H), 8.99 (s, 1H), 8.28 (s, 1H), 7.99 (s, 1H), 7.81 (dd, J=8.2, 1.8 Hz, 1H), 7.77 (s, 1H), 7.40-7.36 (m, 2H), 7.32-7.29 (m, 1H), 7.25 (d, J=7.2 Hz, 1H), 2.59 (q, J=7.5 Hz, 2H), 1.05 (t, J=7.5 Hz, 3H).

Sources & evidence

ORD record
ord-26a67018dbb74c14913a19772100d401
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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