Methyl 9-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylate → Methyl 2-(3-chlorobenzyl)-1,8-dioxo-9-hydroxy-1,3,4,8-tetrahydro-2h-pyrido[1,2-a]pyrazine-7-carboxylate
Reaction equation
C(OC1C(=O)C(Br)=CN2CCN(CC3C=CC=C(Cl)C=3)C(=O)C=12)C1C=CC=CC=1.C([O:37][C:38]1[C:39](=[O:61])[C:40]([C:57]([O:59][CH3:60])=[O:58])=[CH:41][N:42]2[CH2:47][CH2:46][N:45]([CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([Cl:55])[CH:50]=3)[C:44](=[O:56])[C:43]=12)C1C=CC=CC=1>>[Cl:55][C:51]1[CH:50]=[C:49]([CH:54]=[CH:53][CH:52]=1)[CH2:48][N:45]1[CH2:46][CH2:47][N:42]2[CH:41]=[C:40]([C:57]([O:59][CH3:60])=[O:58])[C:39](=[O:61])[C:38]([OH:37])=[C:43]2[C:44]1=[O:56]Participants
Reactant 2
Product 1
Procedure
By subjecting 9-benzyloxy-7-bromo-2-(3-chlorobenzyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (600 mg) produced by the same method as in Example 249, Step 1 to a reaction operation similar to that in Example 161, Step 3, a mixture of methyl 9-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylate and methyl 2-(3-chlorobenzyl)-1,8-dioxo-9-hydroxy-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylate was obtained (13 mg). This mixture was dissolved in dimethylformamide (17 ml) and treated with benzyl bromide (1.36 g) and potassium carbonate (1.75 g) and purified by silica gel column chromatography (ethyl acetate-chloroform:methanol=10:1) to give methyl 9-benzyloxy-2-(3-chlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylate (480 mg).
Workup
- customproduced by the same method as in Example 249, Step 1 to a reaction operation similar to that in Example 161, Step 3
Sources & evidence
- ORD record
- ord-35beb3b9099b4af6a8333c8e64adfadd
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211572B2
Reaction notes
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