3-Chloropropionyl chloride → 2-(Trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine

HRID 1043823

Reaction equation

HRID 1043823 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.ClCCC(Cl)=O>ClCCl>[F:21][C:18]([F:19])([F:20])[C:13]1[CH:12]=[CH:11][C:10]2[CH2:9][NH:8][CH2:17][CH2:16][C:15]=2[N:14]=1

Participants

4

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 577709166-Benzyl-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 1

HCID 534719842-(Trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5 (500 mg, 1.7 mmol) in dichoromethane (8 mL) was added compound 6, 3-chloro propionyl chloride (0.22 mL, 2.1 mmol) and the reaction mixture was stirred at 40° C. for 18 h. The reaction was then cooled to room temperature and concentrated. The resulting residue was dissolved in methanol (16 mL) and stirred at 40° C. for 3 h. The mixture was then cooled to room temperature and concentrated.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in methanol (16 mL)
  4. stirringstirred at 40° C. for 3 h
  5. temperatureThe mixture was then cooled to room temperature
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea0d4bec166348a088b680e664e78c47
Source dataset
uspto-grants-2013_10
Patent number
US08563566B2

Linked notes

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