N-Cyclopropylmethyl-N-(2-ethyl-7-iodopyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine hydrochloride → N-Cyclopropylmethyl-2-ethyl-7-iodo-N-(tetrahydro-2H-pyran-4-ylmethyl)pyrazolo[1,5-a]pyridine-3-amine

HRID 2267198Notes

Reaction equation

HRID 2267198 reaction equation
Cl.[CH:2]1([CH2:5][N:6]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:7]2[C:8]([CH2:17][CH3:18])=[N:9][N:10]3[C:15]([I:16])=[CH:14][CH:13]=[CH:12][C:11]=23)[CH2:4][CH2:3]1.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH:2]1([CH2:5][N:6]([CH2:19][CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:7]2[C:8]([CH2:17][CH3:18])=[N:9][N:10]3[C:15]([I:16])=[CH:14][CH:13]=[CH:12][C:11]=23)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21084143N-Cyclopropylmethyl-N-(2-ethyl-7-iodopyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine hydrochlorideHCID 86585896Sodium bicarbonate water

Product 1

HCID 11339625N-Cyclopropylmethyl-2-ethyl-7-iodo-N-(tetrahydro-2H-pyran-4-ylmethyl)pyrazolo[1,5-a]pyridine-3-amineYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To N-cyclopropylmethyl-2-ethyl-7-iodo-N-(tetrahydro-2H-pyran-4-ylmethyl)pyrazolo[1,5-a]pyridine-3-amine hydrochloride (16 g) was added saturated sodium bicarbonate water (200 mL) to give neutrality. Then, ethyl acetate (100 mL) was added to this, and an organic layer was separated. From the organic layer, the solvent was distilled off under reduced pressure. Into the resulting residue was dropped acetonitrile (30 mL) and water (120 mL), the mixture was stirred overnight, and the resulting precipitate was filtrated. The precipitate was dried under reduced pressure, and 13 g of a title compound was obtained as white crystal.

Workup

  1. customto give neutrality
  2. customwas separated
  3. distillationFrom the organic layer, the solvent was distilled off under reduced pressure
  4. additionInto the resulting residue was dropped acetonitrile (30 mL) and water (120 mL)
  5. filtrationthe resulting precipitate was filtrated
  6. customThe precipitate was dried under reduced pressure

Sources & evidence

ORD record
ord-b19a3fbd708d468ea5ce281b5fdcec74
Source dataset
uspto-grants-2010_12
Patent number
US07858809B2

Reaction notes

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