Water → Ethyl 3-[({[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]amino}carbonyl)amino]propanoate

HRID 469215Notes

Reaction equation

HRID 469215 reaction equation
[N+](C1C=CC([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)=CC=1)([O-])=O.[NH2:21][C:22]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][C:27]([NH:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[C:28]([F:33])[CH:29]=2)[N:24]([CH:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH:23]=1.N1C=CC=CC=1.O>ClCCl>[CH:35]1([NH:34][C:27]2[CH:26]=[C:25]3[C:30]([C:31](=[O:32])[C:22]([NH:21][C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:8])=[CH:23][N:24]3[CH:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[CH:29][C:28]=2[F:33])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 66636675Ethyl 3-{[(4-nitrophenoxy)carbonyl]amino}propanoateHCID 666368863-amino-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one

Product 1

HCID 66636887Ethyl 3-[({[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]amino}carbonyl)amino]propanoateYield 38.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

180 mg of 4-nitrophenyl chloroformate was dissolved in 3.0 ml of dichloromethane, and 140 mg of ethyl 3-aminopropanoate hydrochloride and 0.15 ml of pyridine were added, followed by overnight stirring at room temperature. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and then concentrated under a reduced pressure. By purifying the resulting residue by silica gel column chromatography, 180 mg of ethyl 3-{[(4-nitrophenoxy)carbonyl]amino}propanoate was obtained. 180 mg of ethyl 3-{[(4-nitrophenoxy)carbonyl]amino}propanoate was dissolved in 2.0 ml of dichloromethane, and 220 mg of 3-amino-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one and 0.15 ml of pyridine were added, followed by overnight stirring at room temperature. Water was added, followed by extraction with chloroform. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then filtered and concentrated under a reduced pressure. By purifying the resulting residue by silica gel column chromatography, 120 mg of ethyl 3-[({[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]amino}carbonyl)amino]propanoate was obtained.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under a reduced pressure
  6. customBy purifying the resulting residue by silica gel column chromatography

Sources & evidence

ORD record
ord-9d342e09559744ed9ec4a7945aeab5bc
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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