Water → HCID 70944643, compound

HRID 2401231Notes

Reaction equation

HRID 2401231 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:16][C:17]1[C:22]([F:23])=[C:21]([CH2:24][CH3:25])[N:20]=[CH:19][N:18]=1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[ClH:16].[CH2:24]([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[F:23])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 167434454-Chloro-6-ethyl-5-fluoropyrimidine2×HCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2×

Product 1

HCID 70944643HCID 70944643, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 1-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 50 mg, 0.232 mmol) in dry NMP (2 mL) was treated with 4-chloro-6-ethyl-5-fluoropyrimidine (Intermediate 27, 74.6 mg, 0.465 mmol) and DIPEA (0.081 mL, 0.465 mmol). The reaction mixture was then stirred at room temperature over the weekend. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mL). The organic extract was then washed with water (20 mL×2), dried (MgSO4), filtered and the solvent was removed. The resulting residues were then purified on the MDAP and fractions containing desired product were combined and evaporated to dryness. The resulting residues were then dissolved in methanol (10 mL) and 4M HCl in dioxane (1 mL) was added. The mixture was then evaporated to dryness to give the title compound as an off white solid (45 mg).

Workup

  1. extractionextracted with ethyl acetate (20 mL)
  2. extractionThe organic extract
  3. washwas then washed with water (20 mL×2)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed
  7. customThe resulting residues were then purified on the MDAP and fractions
  8. additioncontaining desired product
  9. customevaporated to dryness
  10. dissolutionThe resulting residues were then dissolved in methanol (10 mL)
  11. addition4M HCl in dioxane (1 mL) was added
  12. customThe mixture was then evaporated to dryness

Sources & evidence

ORD record
ord-2a61fc83e7c541e6a9e4e8ac67d2ac15
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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