Glycine ethyl ester, hydrochloride → HCID 131729495, compound

HRID 469248Notes

Reaction equation

HRID 469248 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:25])[C:13]([CH:23]=O)=[CH:14][N:15]3[CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:27].[NH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].[H][H]>[C].[Pd].C(O)C>[ClH:27].[CH2:33]([O:32][C:30](=[O:31])[CH2:29][NH:28][CH2:23][C:13]1[C:12](=[O:25])[C:11]2[C:16](=[CH:17][C:8]([NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:9]([F:26])[CH:10]=2)[N:15]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:14]=1)[CH3:34]

Participants

6

Reactant 3

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 866330517-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 131729495HCID 131729495, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a 5.0 ml ethanol solution of 500 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde was added 215 mg of ethyl aminoacetate hydrochloride, followed by stirring at room temperature for 2 hours. Next, 50 mg of palladium-carbon was added thereto, followed by stirring at room temperature for 4 hours in an atmosphere of hydrogen. The reaction mixture was filtered through celite and then evaporated under a reduced pressure. The resulting residue was purified by silica gel column chromatography. To a 3.6 ml dioxane solution of the resulting compound was added 4.0 ml of a 4 M hydrogen chloride dioxane solution, followed by overnight stirring at room temperature. The insoluble materials were collected by filtration to obtain 320 mg of ethyl({[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}amino)acetate hydrochloride.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated under a reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography
  4. additionTo a 3.6 ml dioxane solution of the resulting compound was added 4.0 ml of a 4 M hydrogen chloride dioxane solution
  5. waitfollowed by overnight
  6. stirringstirring at room temperature
  7. filtrationThe insoluble materials were collected by filtration

Sources & evidence

ORD record
ord-e8717cc79f984015b94a4d2ce9f2be55
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

Loading…