3-(Methylsulfonyl)phenylboronic acid → HCID 136027603, compound

HRID 1428909Notes

Reaction equation

HRID 1428909 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][S:32]([C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1)(=[O:34])=[O:33]>>[CH3:31][S:32]([C:35]1[CH:40]=[C:39]([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:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33]

Participants

3

Reactant 2

HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 68487682HCID 68487682, compound

Product 1

HCID 136027603HCID 136027603, 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-(methylsulfonyl)phenylboronic acid in step C. MS (ESI): mass calcd. for C19H14N4O5S, 410.1; m/z found, 411.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.01 (br s, 2H), 8.99 (s, 1H), 8.47 (d, J=2.1 Hz, 1H), 8.31-8.27 (m, 3H), 8.18 (d, J=8.5 Hz, 1H), 7.97 (ddd, J=7.8, 1.7, 1.0 Hz, 1H), 7.85 (d, J=7.7 Hz, 1H), 7.80 (t, J=7.8 Hz, 1H), 3.34 (s, 3H).

Sources & evidence

ORD record
ord-1617e2f19ed34244a6c35a5ff7762fe2
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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