N,N-diethylazetidin-3-amine dihydrochloride → 8-(3-Diethylamino-1-azetidinyl)-3-ethoxy-carbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine
Reaction equation
[CH2:1]([O:3][CH:4]1[C:13](=[C:14]=[O:15])[N:12]([CH3:16])[C:11]2[N:10]=[C:9]3[CH:17]=[C:18](F)[C:19]([F:21])=[CH:20][C:8]3=[CH:7][C:6]=2[C:5]1=[O:23])[CH3:2].Cl.Cl.[CH2:26]([N:28]([CH2:33][CH3:34])[CH:29]1[CH2:32][NH:31][CH2:30]1)[CH3:27]>>[CH2:26]([N:28]([CH2:33][CH3:34])[CH:29]1[CH2:32][N:31]([C:18]2[C:19]([F:21])=[CH:20][C:8]3[C:9]([CH:17]=2)=[N:10][C:11]2[N:12]([CH3:16])[C:13](=[C:14]=[O:15])[CH:4]([O:3][CH2:1][CH3:2])[C:5](=[O:23])[C:6]=2[CH:7]=3)[CH2:30]1)[CH3:27]Participants
3
Procedure
8-(3-Diethylamino-1-azetidinyl)-3-ethoxy-carbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 2, but starting with 2 g of 3-ethoxy-carbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine and 1.4 g of 3-(diethylamino)-azetidine dihydrochloride. After recrystallization of the crude product in 500 cm3 of methanol, 2.07 g of 8-(3-diethylamino-1-azetidinyl)-3-ethoxy-carbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine are obtained in the form of a yellow solid, melting point 260° C.
Workup
- customAfter recrystallization of the crude product in 500 cm3 of methanol, 2.07 g of 8-(3-diethylamino-1-azetidinyl)-3-ethoxy-carbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine
- customare obtained in the form of a yellow solid, melting point 260° C.
Sources & evidence
- ORD record
- ord-98b6e52e90ed481485a972f3eddf7798
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556861
Reaction notes
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