Diisopropylethylamine → HCID 51356129, compound

HRID 2401226Notes

Reaction equation

HRID 2401226 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]([CH:23]([F:25])[F:24])[N:20]=[CH:19][N:18]=1.CCN(C(C)C)C(C)C>CN1CCCC1=O.C(OCC)(=O)C>[F:24][CH:23]([F:25])[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 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2×HCID 717433824-chloro-6-(difluoromethyl)pyrimidine2×

Product 1

HCID 51356129HCID 51356129, compoundYield 18.8%

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, 100 mg, 0.465 mmol), 4-chloro-6-(difluoromethyl)pyrimidine (Intermediate 22, 117 mg, 0.711 mmol) and DIPEA (0.162 mL, 0.929 mmol) were added together in N-methyl-2-pyrrolidone (3 mL) and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was 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 (30 mg);

Workup

  1. washwashed with water and brine
  2. customThe organic layer was separated
  3. customdried under magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by MDAP
  6. additionProduct containing fractions
  7. customevaporated under reduced pressure
  8. customThe resulting solid was dried under high vacuum at 45° C. for 18 hours

Sources & evidence

ORD record
ord-4b0d3f25fbe4431c8bf891ac15b9186d
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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