Cyclopropylamine → HCID 68513566, compound

HRID 2063263Notes

Reaction equation

HRID 2063263 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:10][N:11]3[C:16]=2[CH2:15][CH2:14][CH2:13][N:12]3[CH3:17])[CH:5]=[CH:4][N:3]=1.[CH:25]1([NH2:28])[CH2:27][CH2:26]1>CN1CCCC1=O.O>[CH:25]1([NH:28][C:2]2[N:7]=[C:6]([C:8]3[C:9]([C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)=[N:10][N:11]4[C:16]=3[CH2:15][CH2:14][CH2:13][N:12]4[CH3:17])[CH:5]=[CH:4][N:3]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 86646913HCID 86646913, compound2×

Product 1

HCID 68513566HCID 68513566, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-(2-chloro-4-pyrimidinyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydro-7-methylpyrazolo[1,5-b]pyridazine (i.e. the product of Step B) (30.0 mg, 0.087 mmol) and cyclopropylamine (0.31 mL, 4.36 mmol) in 1-methyl-2-pyrrolidinone (2 mL) was heated under microwave irradiation at 150° C. for 30 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by medium pressure liquid chromatography using 20-80% ethyl acetate in hexanes as eluant to give 27 mg of the title product, a compound of the present invention, as a white solid.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by medium pressure liquid chromatography

Sources & evidence

ORD record
ord-3fcfdc5a0a1a4de09b84dc6a6682c44c
Source dataset
uspto-grants-2012_10
Patent number
US08288375B2

Reaction notes

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