Tert-Butylamine → HCID 20063288, compound

HRID 1084412Notes

Reaction equation

HRID 1084412 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Cl[C:7]1[C:16]([C:17]([C:19](=[CH:25]N(C)C)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:18])=[CH:15][C:14]2[C:9](=[C:10]([F:31])[C:11]([F:30])=[C:12]([F:29])[CH:13]=2)[N:8]=1.C1CCN2C(=NCCC2)CC1>ClC(Cl)Cl.C(O)C>[CH2:23]([O:22][C:20]([C:19]1[C:17](=[O:18])[C:16]2[CH:15]=[C:14]3[CH:13]=[C:12]([F:29])[C:11]([F:30])=[C:10]([F:31])[C:9]3=[N:8][C:7]=2[N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:25]=1)=[O:21])[CH3:24]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53994177Ethyl 2-(2-chloro-6,7,8-trifluoro-3-quinolinecarbonyl)(dimethylamino)acrylate

Product 1

HCID 20063288HCID 20063288, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

9.5 g of tert.-butylamine are added at a temperature of about 20° C., in the course of 5 minutes, to a stirred solution of 11.7 g of ethyl 2-(2-chloro- 6,7,8-trifluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate in 150 cm3 of trichloromethane at the same temperature. After stirring for 4 hours at about 20° C., the solution is concentrated to dryness under reduced pressure (20 kPa) at about 50° C. The residue obtained is taken up in 100 cm3 of ethanol. 5 g of DBU are added to the solution obtained and the mixture is heated at a temperature close to 75° C. for 3 hours. After cooling to about 20° C., the precipitate obtained is drained and washed with twice 50 cm3 of ethanol and twice 50 cm3 of diisopropyl ether. 9.5 g of 3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1-tert.-butyl-1,4-dihydro-benzo[b][1,8]naphthyridine are obtained in the form of a colourless solid melting at 229° C., which is used for the subsequent steps without further purification.

Workup

  1. concentrationthe solution is concentrated to dryness under reduced pressure (20 kPa) at about 50° C
  2. customThe residue obtained
  3. customobtained
  4. temperaturethe mixture is heated at a temperature
  5. customclose to 75° C. for 3 hours
  6. temperatureAfter cooling to about 20° C.
  7. customthe precipitate obtained
  8. washwashed with twice 50 cm3 of ethanol and twice 50 cm3 of diisopropyl ether

Sources & evidence

ORD record
ord-1e95f25573134b61b693a4c9c8da423d
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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