Cyclopropanemethanamine → N-Cyclopropylmethyl-[4-[6-[3-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-5-yl]pyrimidin-2-yl]amine

HRID 42609Notes

Reaction equation

HRID 42609 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[CH:29]=[N:28][NH:27][C:14]3=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH:30]1([CH2:33][NH2:34])[CH2:32][CH2:31]1>C1COCC1>[CH:30]1([CH2:33][NH:34][C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[C:13]4[CH:29]=[N:28][NH:27][C:14]4=[N:15][C:16]=3[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=3)[CH:8]=[CH:7][N:6]=2)[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 670138055-[2-(methylsulfonyl)pyrimidin-4-yl]-6-[3-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 68445187N-Cyclopropylmethyl-[4-[6-[3-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-5-yl]pyrimidin-2-yl]amineYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-[2-(methylsulfonyl)pyrimidin-4-yl]-6-[3-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-b]pyridine (90 mg, 0.2 mmol, obtained in example 127) and (cyclopropylmethyl)amine (75 mg, 1.0 mmol) in THF (2 mL) was heated in a closed vessel at 60° C. overnight. It was allowed to cool and concentrated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 57 mg of the desired compound (yield: 67%).

Workup

  1. temperatureto cool
  2. concentrationconcentrated
  3. customThe crude product obtained
  4. customwas purified by chromatography on silica gel
  5. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-069d336c5da540d9a78788420720faa9
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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