(2H-1,3-benzodioxol-5-yl)boronic acid → HCID 136027638, compound

HRID 1428910Notes

Reaction equation

HRID 1428910 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]1[O:39][C:38]2[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][C:33]=2[O:32]1>>[O:32]1[C:33]2[CH:34]=[CH:35][C:36]([C:16]3[CH:17]=[C:18]4[C:13](=[CH:14][CH:15]=3)[N:12]=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]3)[NH:20][C:19]4=[O:29])=[CH:37][C:38]=2[O:39][CH2:31]1

Participants

3

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 68487682HCID 68487682, compound

Product 1

HCID 136027638HCID 136027638, 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 3,4-methylenedioxyphenylboronic acid in step C. (ESI): mass calcd. for C19H12N4O5, 376.1; m/z found, 377.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.96 (br s, 2H), 8.97 (s, 1H), 8.29-8.25 (m, 2H), 8.11 (dd, J=8.5, 2.2 Hz, 1H), 7.75 (d, J=8.5 Hz, 1H), 7.38 (d, J=1.7 Hz, 1H), 7.27 (dd, J=8.1, 1.8 Hz, 1H), 7.05 (d, J=8.1 Hz, 1H), 6.10 (s, 2H).

Sources & evidence

ORD record
ord-a81289c3ad7748c2aeba8d8b1fcc2b59
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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