2-Morpholinoethanol → HCID 9829665, compound

HRID 2293976Notes

Reaction equation

HRID 2293976 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:29])=[C:10]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[N:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:19][CH2:18]3)[C:11]=2[O:13][CH:14]([F:16])[F:15])[C:6](=[O:30])[C:5]([C:31]([OH:33])=[O:32])=[CH:4]1)[CH3:2].O[CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH3:3].[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:29])=[C:10]([N:17]3[CH2:18][CH2:19][N:20]([C:23]4[N:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:21][CH2:22]3)[C:11]=2[O:13][CH:14]([F:16])[F:15])[C:6](=[O:30])[C:5]([C:31]([O:33][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=[O:32])=[CH:4]1)[CH3:2]

Participants

7

Reactant 3

HCID 611632-MorpholinoethanolHCID 469670HCID 469670, compoundHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 2

HCID 222AmmoniaYield 28%HCID 9829665HCID 9829665, compoundYield 137.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 3 l of methylene chloride were added 58.94 g (0.127 mole) of 1-ethyl-6-fluoro-8-difluoromethoxy-7-[4-(2-pyrimidinyl)piperazin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 25.05 g (0.191 mole) of 4-(2-hydroxyethyl)morpholine, 23.3 g (0.191 mole) of 4-dimethylaminopyridine and 48.8 g (0.254 mole) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and the mixture was stirred at room temperature for 4 days. Then, the solvent was removed under reduced pressure. The residue was dissolved in chloroform, washed with a 1N hydrochloric acid aqueous solution, washed with water and dried. The solvent was removed under reduced pressure, and the residue was applied to silica gel column chromatography (the eluent used was a mixture of chloroform: methanol: 28% aqueous ammonia=40:9:1) to obtain 50.25 g of the title compound as slightly yellowish white powder.

Workup

  1. customThen, the solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with a 1N hydrochloric acid aqueous solution
  4. washwashed with water
  5. customdried
  6. customThe solvent was removed under reduced pressure
  7. additiona mixture of chloroform

Sources & evidence

ORD record
ord-f4bb3784b81e4befbd59e87fb8f8b3db
Source dataset
uspto-grants-1997_11
Patent number
US05688791

Reaction notes

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