Hydrochloric Acid → HCID 69483561, compound

HRID 2233006Notes

Reaction equation

HRID 2233006 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(OC(=O)[NH:22][CH2:23][CH2:24][NH2:25])(C)(C)C.Cl>O1CCOCC1>[F:13][C:12]([F:15])([F:14])[C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:22][CH2:23][CH2:24][NH2:25])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 187201N-BOC-ethylenediamine

Product 1

HCID 69483561HCID 69483561, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 120 mg of 4-chloro-7-trifluoromethylquinoline and 250 mg of tert-butyl-N-(2-aminoethyl)carbamate was heated to 125° C. for two h. The mixture was cooled to room temperature and partitioned between 10% IPA/chloroform and saturated sodium bicarbonate. The aqueous layer was back extracted with 10% IPA/chloroform and the organic layers were dried over sodium sulfate, filtered and concentrated. The residue was dissolved in EtOAc and washed with water, and the organic layer was dried over sodium sulfate, filtered, and concentrated. The product was dissolved in MeOH (0.5 mL) and stirred with five equiv. of 4.0 M HCl in dioxane for 18 h. The reaction mixture was concentrated and the residue was recrystallized from MeOH to afford the title compound. MS (M+H)+=256.1.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between 10% IPA/chloroform and saturated sodium bicarbonate
  3. extractionThe aqueous layer was back extracted with 10% IPA/chloroform
  4. dry with materialthe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in EtOAc
  8. washwashed with water
  9. dry with materialthe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. dissolutionThe product was dissolved in MeOH (0.5 mL)
  13. concentrationThe reaction mixture was concentrated
  14. customthe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-64ecb9b2d5894271a7c9476e5cd50020
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

Loading…