2-Chlorophenylboronic acid → HCID 136027578, compound

HRID 1428888Notes

Reaction equation

HRID 1428888 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:60]=[CH:59][CH:58]=[CH:57][C:56]=1B(O)O>>[Cl:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[C:15]1[CH:14]=[C:13]2[C:18]([C:19](=[O:27])[NH:20][C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]3)=[N:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 27343222-Chlorophenylboronic acidHCID 68486204HCID 68486204, compoundHCID 136027561HCID 136027561, compound

Product 1

HCID 136027578HCID 136027578, 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 2-chlorophenylboronic acid in step C. MS (ESI): mass calcd. for C18H11ClN4O3, 366.1; m/z found, 367.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 13.02 (br s, 1H), 12.92 (br s, 1H), 8.97 (s, 1H), 8.28 (s, 1H), 8.22 (d, J=6.6 Hz, 1H), 7.71 (s, 1H), 7.67-7.62 (m, 1H), 7.58 (d, J=7.3 Hz, 1H), 7.55-7.47 (m, 3H).

Sources & evidence

ORD record
ord-327c71950757467f99ee9c5413957d4c
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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