(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid → HCID 23509597, compound

HRID 50724Notes

Reaction equation

HRID 50724 reaction equation
[CH3:1][C:2]1([CH3:16])[C:7]2[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:15])[O:3]1.Br[C:18]1[CH:19]=[C:20]([C:24]2[N:28]=[CH:27][S:26][N:25]=2)[CH:21]=[CH:22][CH:23]=1>>[S:26]1[CH:27]=[N:28][C:24]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:18][C:19]=2[C:9]2[CH:10]=[CH:11][C:6]3[NH:5][C:4](=[O:15])[O:3][C:2]([CH3:16])([CH3:1])[C:7]=3[CH:8]=2)=[N:25]1

Participants

3

Reactant 2

HCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acidHCID 23509622HCID 23509622, compound

Product 1

HCID 23509597HCID 23509597, compoundYield 35%

Procedure

According to procedure B, (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid was coupled with 3-[3-bromo-phenyl]-[1,2,4]thiadiazole to yield 6-(1,2,4-thiadiazol-3-yl-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]-oxazin-2-one as an off-white solid (0.5 g, 35%): mp 214-216° C.; 1H-NMR (DMSO-d6) δ 10.40 (s, 1H), 10.36 (s, 1H), 8.49 (s, 1H), 8.23 (d, 1H, J=7.7 Hz), 7.83 (d, 1H, J=7.9 Hz), 7.66-7.61 (m, 3H), 7.02 (t, 1H, J=4.4 Hz), 1.70 (s, 6H); MS ((+)APCI) [M+H]+@ m/z 338.

Sources & evidence

ORD record
ord-ca25345dacbd4a0ba29bfa190eb523df
Source dataset
uspto-grants-2004_03
Patent number
US06713478B2

Reaction notes

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