Hydrochloric Acid → Isopropanol

HRID 2267192Notes

Reaction equation

HRID 2267192 reaction equation
[CH:1]1([CH2:4][N:5]([C:13]2[C:14]([CH2:23][CH3:24])=[N:15][N:16]3[C:21]([I:22])=[CH:20][CH:19]=[CH:18][C:17]=23)[CH2:6][CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[ClH:25].C(=O)(OC)[O:27]C>C(O)(C)C>[ClH:25].[CH:1]1([CH2:4][N:5]([C:13]2[C:14]([CH2:23][CH3:24])=[N:15][N:16]3[C:21]([I:22])=[CH:20][CH:19]=[CH:18][C:17]=23)[CH2:6][CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[CH:12]([OH:27])([CH3:11])[CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12021Dimethyl Carbonate3×HCID 11339625N-Cyclopropylmethyl-2-ethyl-7-iodo-N-(tetrahydro-2H-pyran-4-ylmethyl)pyrazolo[1,5-a]pyridine-3-amine

Product 2

HCID 3776IsopropanolYield 93.7%HCID 21084143N-Cyclopropylmethyl-N-(2-ethyl-7-iodopyrazolo[1,5-a]pyridin-3-yl)-N-tetrahydro-2H-4-pyranylmethylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Into a solution of N-cyclopropylmethyl-N-(2-ethyl-7-iodopyrazolo[1,5-a]pyridin e-3-yl)-N-(tetrahydro-2H-4-pyranylmethyl)amine (220 g, 501 mmol) in dimethyl carbonate (3600 mL) was dropped a solution of concentrated hydrochloric acid (48.5 mL, 575 mmol) in isopropanol (270 mL) at room temperature over a period of 20 minutes, and the mixture was further stirred at room temperature for about 15 hours. The reaction mixture was cooled in an ice water bath, and to the reaction mixture was added dimethyl carbonate (900 mL). This mixture was stirred for about 5 hours, and a precipitate was filtrated. The precipitate was washed with dimethyl carbonate (900 mL), and dried at 50° C. under reduced pressure, to obtain 250 g of a title compound as a solvate in dimethyl carbonate and isopropanol (yield: 93.7%).

Workup

  1. temperatureThe reaction mixture was cooled in an ice water bath
  2. stirringThis mixture was stirred for about 5 hours
  3. filtrationa precipitate was filtrated
  4. washThe precipitate was washed with dimethyl carbonate (900 mL)
  5. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-7596db0fae704709a2e2478791fc24bd
Source dataset
uspto-grants-2010_12
Patent number
US07858809B2

Reaction notes

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