Diisopropylethylamine → HCID 51356425, compound

HRID 2401238Notes

Reaction equation

HRID 2401238 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[C:22]([CH3:23])=[C:21]([CH:24]([F:26])[F:25])[N:20]=[CH:19][N:18]=1.CCN(C(C)C)C(C)C>CN(C)C=O.C(OCC)(=O)C>[F:25][CH:24]([F:26])[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)[C:22]=1[CH3:23]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 178565454-Chloro-6-(difluoromethyl)-5-methylpyrimidineHCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2×

Product 1

HCID 51356425HCID 51356425, compoundYield 22.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 100 mg, 0.465 mmol), 4-chloro-6-(difluoromethyl)-5-methylpyrimidine (ANICHEM CAS425394-59-8, 83 mg, 0.465 mmol) and DIPEA (0.162 mL, 0.929 mmol) were added together in N,N-dimethylformamide (5 mL) and the resulting mixture was stirred at room temperature for overnight. 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 (38 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-2ffa81c3c8c3441c80b1e51144d7a2b1
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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