3-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine → (RS)-3-Ethoxycarbonyl-7,9-difluoro-8-{3-[4-(2-hydroxyethoxy)phenyl]-1-piperazinyl}-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 344912Notes

Reaction equation

HRID 344912 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18](F)=[C:17]([F:23])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2].[OH:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]2[CH2:40][NH:39][CH2:38][CH2:37][NH:36]2)=[CH:31][CH:30]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([N:39]4[CH2:38][CH2:37][NH:36][CH:35]([C:32]5[CH:31]=[CH:30][C:29]([O:28][CH2:27][CH2:26][OH:25])=[CH:34][CH:33]=5)[CH2:40]4)=[C:17]([F:23])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 194236883-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 54120210(RS)-2-[4-(2-hydroxyethoxy)phenyl]piperazine

Product 1

HCID 53945605(RS)-3-Ethoxycarbonyl-7,9-difluoro-8-{3-[4-(2-hydroxyethoxy)phenyl]-1-piperazinyl}-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Procedure

(RS)-3-Ethoxycarbonyl-7,9-difluoro-8-{3-[4-(2-hydroxyethoxy)phenyl]-1-piperazinyl}-1 -methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 39, but starting with 3-ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.9 g) and (RS)-2-[4-(2-hydroxyethoxy)phenyl]piperazine (1.6 g). The expected product (2.2 g) is obtained in the form of a yellow solid, m.p. 183° C.

Sources & evidence

ORD record
ord-2c8910df404945679b659fa53d4779db
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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