Choline, hydroxide → HCID 18549169, compound

HRID 1266164Notes

Reaction equation

HRID 1266164 reaction equation
[F:1][C:2]1[C:20]([N:21]2[CH2:26][CH2:25][CH:24]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.[OH-].[OH:36][CH2:37][CH2:38][N+:39]([CH3:42])([CH3:41])[CH3:40]>CO>[OH:36][CH2:37][CH2:38][N+:39]([CH3:42])([CH3:41])[CH3:40].[F:1][C:2]1[C:20]([N:21]2[CH2:22][CH2:23][CH:24]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[CH2:25][CH2:26]2)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([O-:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 31255Choline, hydroxideHCID 9912270HCID 9912270, compound

Product 1

HCID 18549169HCID 18549169, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Choline 7-fluoro-8-[4-(4-fluoroanilino)piperidino]-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylate was prepared under the conditions of Example 1, but from 1.6 g of 7-fluoro-8-[4-(4-fluoroanilino)piperidino]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid in 16 cm3 of methanol and 1.3 cm3 of a 45% solution of choline hydroxide in methanol. After recrystallizing twice from 25 cm3 of 2-propanol on each occasion, 1.1 g of choline 7-fluoro-8-[4-(4-fluoroanilino)piperidino]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate were obtained in the form of a yellow solid melting at about 200-205° C.

Workup

  1. customCholine 7-fluoro-8-[4-(4-fluoroanilino)piperidino]-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylate was prepared under the conditions of Example 1
  2. customAfter recrystallizing twice from 25 cm3 of 2-propanol on each occasion

Sources & evidence

ORD record
ord-0a319bfcfb95492c9964e9db1eb87a32
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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