Hydrochloric Acid → N-Cyclopropylmethyl-N-(2-ethyl-7-iodopyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine hydrochloride

HRID 347864Notes

Reaction equation

HRID 347864 reaction equation
[ClH:1].[CH:2]1([CH2:5][N:6]([C:14]2[C:15]([CH2:24][CH3:25])=[N:16][N:17]3[C:22]([I:23])=[CH:21][CH:20]=[CH:19][C:18]=23)[CH2:7][CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH2:4][CH2:3]1>C(O)(C)C.C(=O)(OC)OC>[ClH:1].[CH:2]1([CH2:5][N:6]([C:14]2[C:15]([CH2:24][CH3:25])=[N:16][N:17]3[C:22]([I:23])=[CH:21][CH:20]=[CH:19][C:18]=23)[CH2:7][CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11339625N-Cyclopropylmethyl-2-ethyl-7-iodo-N-(tetrahydro-2H-pyran-4-ylmethyl)pyrazolo[1,5-a]pyridine-3-amine

Product 1

HCID 21084143N-Cyclopropylmethyl-N-(2-ethyl-7-iodopyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine hydrochlorideYield 104.9%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 12021Dimethyl CarbonateSolvent3×

Procedure

A solution of concentrated hydrochloric acid (48.5 mL, 575 mmol) in isopropanol (270 mL) was added dropwise to a solution of N-cyclopropylmethyl-N-(2-ethyl-7-iodopyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine (220 g, 501 mmol) in dimethyl carbonate (3600 mL) over a period of 20 minutes at room temperature, and the reaction mixture was stirred for 15 hours at room temperature. The reaction mixture was then cooled in an ice water bath, and dimethyl carbonate (900 mL) was added thereto. After stirring the reaction mixture for about 5 hours, the precipitated solid was collected by filtration and washed with dimethyl carbonate (900 mL). It was then dried under reduced pressure at 50° C. to afford 250 g of the title compound (93.7% yield) as a solvate with dimethyl carbonate and isopropanol.

Workup

  1. temperatureThe reaction mixture was then cooled in an ice water bath
  2. stirringAfter stirring the reaction mixture for about 5 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with dimethyl carbonate (900 mL)
  5. customIt was then dried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-1e1b5ba396a1494ab49e2ce4a0f79ca5
Source dataset
uspto-grants-2007_02
Patent number
US07176216B2

Reaction notes

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