Diisopropylethylamine → HCID 51356130, compound

HRID 2401227Notes

Reaction equation

HRID 2401227 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[NH:13][C:6]2=[N:7][CH:8]=[C:9]([CH2:11][NH2:12])[CH:10]=[C:5]2[CH:4]=1.Cl[C:17]1[CH:22]=[C:21]([CH2:23][F:24])[N:20]=[CH:19][N:18]=1.CCN(C(C)C)C(C)C>CN1CCCC1=O.C(OCC)(=O)C>[F:24][CH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]([NH:12][CH2:11][C:9]2[CH:10]=[C:5]3[CH:4]=[C:3]([C:2]([F:1])([F:14])[F:15])[NH:13][C:6]3=[N:7][CH:8]=2)[CH:22]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 337354984-Chloro-6-(fluoromethyl)pyrimidine2×HCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2×

Product 1

HCID 51356130HCID 51356130, compoundYield 8.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 65 mg, 0.211 mmol), 4-chloro-6-(fluoromethyl)pyrimidine (Intermediate 26, 40 mg, 0.232 mmol) and DIPEA (0.074 mL, 0.423 mmol) were added together in N-methyl-2-pyrrolidone (2 mL) and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was heated at 100° C. for 3 hours, allowed to cool to room temperature and diluted with ethyl acetate and washed with water and brine. The organic layer was separated, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by MDAP. Product containing fractions were combined and evaporated under reduced pressure. The resulting solid was dried under high vacuum at 45° C. for 18 hours to give the title compound as a white solid (6 mg);

Workup

  1. temperatureThe reaction mixture was heated at 100° C. for 3 hours
  2. temperatureto cool to room temperature
  3. washwashed with water and brine
  4. customThe organic layer was separated
  5. customdried under magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by MDAP
  8. additionProduct containing fractions
  9. customevaporated under reduced pressure
  10. customThe resulting solid was dried under high vacuum at 45° C. for 18 hours

Sources & evidence

ORD record
ord-2bdc13ff339643408ec6d8c66dcb73be
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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