3-Tolylboronic acid → HCID 136027633, compound

HRID 1428892Notes

Reaction equation

HRID 1428892 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:20](COCCOC)[C:19](=[O:27])[C:18]3[C:13](=[CH:14][C:15](I)=[CH:16][CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.O=C1[C:39]2[C:34](=[CH:35][C:36]([C:40]3C=CC=CC=3)=[CH:37][CH:38]=2)N=C(N2C=C(C(O)=O)C=N2)N1.CC1C=C(B(O)O)C=CC=1>>[O:27]=[C:19]1[C:18]2[C:13](=[CH:14][C:15]([C:34]3[CH:35]=[C:36]([CH3:40])[CH:37]=[CH:38][CH:39]=3)=[CH:16][CH:17]=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]1

Participants

4

Reactant 3

HCID 27339503-Tolylboronic acidHCID 68486204HCID 68486204, compoundHCID 136027561HCID 136027561, compound

Product 1

HCID 136027633HCID 136027633, compound

Procedure

The titled compound was prepared in a manner analogous to Example 184, steps C-E using 1-[7-iodo-3-(2-methoxy-ethoxymethyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (Intermediate from Example 184, product from step B) and 3-methylphenylboronic acid in step C. MS (ESI): mass calcd. for C19H14N4O3, 346.1; m/z found, 347.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.04 (s, 1H), 12.87 (s, 1H), 8.98 (s, 1H), 8.28 (s, 1H), 8.20 (d, J=8.2 Hz, 1H), 7.94 (s, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.67 (s, 1H), 7.62 (d, J=7.0 Hz, 1H), 7.43 (t, J=7.6 Hz, 1H), 7.29 (d, J=7.5 Hz, 1H), 2.42 (s, 3H).

Sources & evidence

ORD record
ord-c1f33e01670c406ea7229a5074582a56
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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