2-Morpholinoethanol → HCID 15887896, compound

HRID 1636278Notes

Reaction equation

HRID 1636278 reaction equation
C1([C:4]2[NH:5][C:6]3[C:11]([C:12](=[O:17])[C:13]=2[C:14]([OH:16])=[O:15])=[CH:10][C:9]([F:18])=[C:8]([N:19]2[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH2:21][CH2:20]2)[C:7]=3[C:31]([F:34])([F:33])[F:32])CC1.O[CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.Cl.C(N=C=N[CH2:50][CH2:51][CH2:52]N(C)C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH3:5].[O:41]1[CH2:42][CH2:43][N:38]([CH2:37][CH2:36][O:16][C:14]([C:13]2[C:12](=[O:17])[C:11]3[C:6](=[C:7]([C:31]([F:34])([F:32])[F:33])[C:8]([N:19]4[CH2:24][CH2:23][N:22]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=5)[CH2:21][CH2:20]4)=[C:9]([F:18])[CH:10]=3)[N:5]([CH:51]3[CH2:52][CH2:50]3)[CH:4]=2)=[O:15])[CH2:39][CH2:40]1

Participants

7

Reactant 3

HCID 611632-MorpholinoethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19350769HCID 19350769, compound

Product 2

HCID 222AmmoniaYield 28%HCID 15887896HCID 15887896, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 5 ml of methylene chloride were added 100 mg (0.21 mmole) of 2-cyclopropyl-6-fluoro-8-trifluoromethyl-1,4-dihydro-4-oxo-7-[4-(2-pyridyl)piperazin-1-yl]quinoline-3-carboxylic acid, 0-055 g (0.42 mmole) of 4-(2-hydroxyethyl)morpholine, 0.045 g (0.37 mmole) of 4-dimethylaminopyridine and 0.091 g (0.48 mmole) of 1-ethyl-3-(3-dimethyaminopropyl)carbodiimide hydrochloride, the mixture was left to stand at room temperature for 7 days, and then the solvent was removed by evaporation under reduced pressure. The residue was applied to column chromatography (eluent; a chloroform:methanol:28% aqueous ammonia=40:9:1 mixed solution) to obtain 60 mg of 1-cyclopropyl-6-fluoro-8-trifluoromethyl-1,4-dihydro-4-oxo-7-[4-(2-pyridyl)piperazin-1-yl]quinoline-3-carboxylic acid 2-morpholinoethyl ester as pale yellow powder.

Workup

  1. waitthe mixture was left
  2. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ff569b5f519a4b28b1a7617a90befba3
Source dataset
uspto-grants-2000_03
Patent number
US06034086

Reaction notes

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