Ethyl isocyanate → trans-N-ethyl-N'-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}urea

HRID 1639879Notes

Reaction equation

HRID 1639879 reaction equation
[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][NH2:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[N:16]([CH2:19][CH3:20])=[C:17]=[O:18]>O1CCCC1>[CH2:19]([NH:16][C:17]([NH:14][CH2:13][C@@H:11]1[CH2:12][C@H:10]1[C:6]1[C:5]2[N:4]([N:3]=[C:2]([CH3:1])[CH:15]=2)[CH:9]=[CH:8][CH:7]=1)=[O:18])[CH3:20]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 59334541trans-1-[2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine

Product 1

HCID 66720812trans-N-ethyl-N'-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}ureaYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-1-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine (100 mg, 0.497 mmol) in tetrahydrofuran (5 mL) was added isocyanatoethane (43.3 μL, 0.547 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 10 min. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=3/97→15/85) and recrystallization (ethyl acetate/hexane) to give the title compound (52.0 mg, yield 38%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 10 min
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=3/97→15/85) and recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1ee952b40e5b455bb3ca6d7f9dd77ba9
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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