7-Bromo-4-methyl-4H-pyrido[3,2-b][1,4]oxazin-3-one → 4-[5-fluoro-3-(4-methyl-3-oxo-2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-7-ylthio)phenyl]-4-methoxytetrahydropyran

HRID 1492155Notes

Reaction equation

HRID 1492155 reaction equation
Br[C:2]1[CH:11]=[N:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[CH2:6][O:5][C:4]=2[CH:3]=1.[F:14][C:15]1[CH:16]=[C:17]([SH:29])[CH:18]=[C:19]([C:21]2([O:27][CH3:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:20]=1>>[F:14][C:15]1[CH:16]=[C:17]([S:29][C:2]2[CH:11]=[N:10][C:9]3[N:8]([CH3:12])[C:7](=[O:13])[CH2:6][O:5][C:4]=3[CH:3]=2)[CH:18]=[C:19]([C:21]2([O:27][CH3:28])[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[CH:20]=1

Participants

3

Reactant 2

HCID 159259847-Bromo-4-methyl-4H-pyrido[3,2-b][1,4]oxazin-3-oneHCID 189962874-(5-Fluoro-3-mercaptophenyl)-4-methoxytetrahydropyran

Product 1

HCID 189520694-[5-fluoro-3-(4-methyl-3-oxo-2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-7-ylthio)phenyl]-4-methoxytetrahydropyranYield 4%

Procedure

Using the procedure described in Example 11, 7-bromo-4-methyl-2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-3-one was reacted with 4-(5-fluoro-3-mercaptophenyl)-4-methoxytetrahydropyran to give 4-[5-fluoro-3-(4-methyl-3-oxo-2,3-dihydro-4H-pyrido[3,2-b]-[1,4]oxazin-7-ylthio)phenyl]-4-methoxytetrahydropyran in 4% yield, m.p. 127°-128° C.

Sources & evidence

ORD record
ord-bb436fb8c3cc4988af545af6c677ee36
Source dataset
uspto-grants-1994_12
Patent number
US05373007

Reaction notes

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