(3-Chlorophenyl)boronic acid → HCID 136027558, compound

HRID 1428889Notes

Reaction equation

HRID 1428889 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=C1C2C(=CC(C3C=CC=CC=3)=CC=2)N=C(N2C=C(C(O)=O)C=N2)N1.[Cl:54][C:55]1[CH:56]=[C:57](B(O)O)[CH:58]=[CH:59][CH:60]=1>>[Cl:54][C:55]1[CH:60]=[C:59]([C:15]2[CH:14]=[C:13]3[C:18]([C:19](=[O:27])[NH:20][C:11]([N:9]4[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]4)=[N:12]3)=[CH:17][CH:16]=2)[CH:58]=[CH:57][CH:56]=1

Participants

4

Reactant 3

HCID 2734323(3-Chlorophenyl)boronic acidHCID 68486204HCID 68486204, compoundHCID 136027561HCID 136027561, compound

Product 1

HCID 136027558HCID 136027558, 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-chlorophenylboronic acid in step C. MS (ESI): mass calcd. for C18H11ClN4O3, 366.1; m/z found, 367.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 13.04 (br s, 1H), 12.94 (br s, 1H), 8.97 (s, 1H), 8.28 (s, 1H), 8.21 (d, J=8.0 Hz, 1H), 8.00 (s, 1H), 7.91 (s, 1H), 7.87 (d, J=8.4 Hz, 1H), 7.82 (d, J=6.7 Hz, 1H), 7.60-7.52 (m, 2H).

Sources & evidence

ORD record
ord-b369f3caa44c4a0ea81e3d2dfe8b2568
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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