(3-Chlorophenyl)boronic acid → HCID 136027585, compound

HRID 1428896Notes

Reaction equation

HRID 1428896 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.[Cl:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1>>[Cl:31][C:32]1[CH:37]=[C:36]([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:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 68487682HCID 68487682, compound

Product 1

HCID 136027585HCID 136027585, 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-chlorophenylboronic acid in step C. MS (ESI): mass calcd. for C18H11ClN4O3, 366.1; m/z found, 367.0 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.00 (br s, 2H), 8.98 (s, 1H), 8.36 (d, J=2.2 Hz, 1H), 8.28 (s, 1H), 8.20 (dd, J=8.5, 2.3 Hz, 1H), 7.85 (t, J=1.9 Hz, 1H), 7.81-7.75 (m, 2H), 7.55 (t, J=7.9 Hz, 1H), 7.49 (ddd, J=8.0, 2.0, 1.0 Hz, 1H).

Sources & evidence

ORD record
ord-cfb4f94552744cf496186e621c651812
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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