7-Methoxy-1,2-dihydroquinoxalin-2-one → 3-(7-methoxy-2-oxo-2H-quinoxalin-1-ylmethyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1890437Notes

Reaction equation

HRID 1890437 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[C:14]([O:18][C:19]([N:21]1[CH2:24][CH:23]([CH2:25]OS(C)(=O)=O)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([O:18][C:19]([N:21]1[CH2:24][CH:23]([CH2:25][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[N:7]=[CH:8][C:9]2=[O:13])[CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

3

Reactant 2

HCID 4913197-Methoxy-1,2-dihydroquinoxalin-2-oneHCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

Product 1

HCID 671308673-(7-methoxy-2-oxo-2H-quinoxalin-1-ylmethyl)-azetidine-1-carboxylic acid tert-butyl esterYield 35.7%

Procedure

Using the procedure of Example 2, step 2.i, but starting from 7-methoxy-2(1H)-quinoxalinone (1.00 g; prepared according to WO 2006/134378) and 3-[[(methylsulfonyl)oxy]methyl]-1-azetidinecarboxylic acid tert-butyl ester (1.65 g; prepared according to WO 02/066470), the second eluting compound was isolated as a yellow oil (700 mg, 35% yield).

Sources & evidence

ORD record
ord-a36b14d8feac4a84bbd60456c9333f2d
Source dataset
uspto-grants-2013_08
Patent number
US08507478B2

Reaction notes

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