2,3-Dihydro-1,4-benzodioxin-5-ylboronic acid → HCID 136027660, compound

HRID 1428907Notes

Reaction equation

HRID 1428907 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.[O:31]1[C:36]2[CH:37]=[CH:38][CH:39]=[C:40](B(O)O)[C:35]=2[O:34][CH2:33][CH2:32]1>>[O:31]1[C:36]2[CH:37]=[CH:38][CH:39]=[C:40]([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])[C:35]=2[O:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 46831952,3-Dihydro-1,4-benzodioxin-5-ylboronic acidHCID 68487682HCID 68487682, compound

Product 1

HCID 136027660HCID 136027660, 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 1,4-benzodioxan-5-boronic acid in step C. MS (ESI): mass calcd. for C20H14N4O5, 390.1; m/z found, 391.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.00 (s, 1H), 12.87 (s, 1H), 8.97 (s, 1H), 8.25 (s, 2H), 8.10 (d, J=7.8 Hz, 1H), 7.73 (s, 1H), 7.28-7.24 (m, 2H), 6.99 (d, J=8.4 Hz, 1H), 4.30 (s, 4H).

Sources & evidence

ORD record
ord-4f420c2f87e24f8893ef2ef4e349181b
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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