Choline, hydroxide → Choline 8-[(cyclohexyl)(methyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate

HRID 1266160Notes

Reaction equation

HRID 1266160 reaction equation
[CH:1]1([N:7]([CH3:28])[C:8]2[C:9]([F:27])=[CH:10][C:11]3[C:12]([CH:26]=2)=[N:13][C:14]2[N:15]([CH3:25])[CH:16]=[C:17]([C:22]([OH:24])=[O:23])[C:18](=[O:21])[C:19]=2[CH:20]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[OH:30][CH2:31][CH2:32][N+:33]([CH3:36])([CH3:35])[CH3:34]>CO>[OH:30][CH2:31][CH2:32][N+:33]([CH3:36])([CH3:35])[CH3:34].[CH:1]1([N:7]([CH3:28])[C:8]2[C:9]([F:27])=[CH:10][C:11]3[C:12]([CH:26]=2)=[N:13][C:14]2[N:15]([CH3:25])[CH:16]=[C:17]([C:22]([O-:24])=[O:23])[C:18](=[O:21])[C:19]=2[CH:20]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 31255Choline, hydroxideHCID 99299188-[(Cyclohexyl)(methyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 18549166Choline 8-[(cyclohexyl)(methyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Choline 8-[(cyclohexyl)(methyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate was prepared under the conditions of Example 1, but from 1.5 g of 8-[(cyclohexyl)(methyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid in 15 cm3 of methanol and 1.5 cm3 of a 45% solution of choline hydroxide in methanol. After recrystallizing from 15 cm3 of 2-propanol, choline 8-[(cyclohexyl)(methyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate was obtained in the form of a yellow solid melting at about 245-250° C.

Workup

  1. customCholine 8-[(cyclohexyl)(methyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate was prepared under the conditions of Example 1
  2. customAfter recrystallizing from 15 cm3 of 2-propanol

Sources & evidence

ORD record
ord-fdf47f0012054b9a9c73ef801c1a454b
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

Loading…