Hydrochloric Acid → (R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxy-3-methylazetidine-1-carboxamide hydrochloride

HRID 588543Notes

Reaction equation

HRID 588543 reaction equation
CO.[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]1[CH:21]=[CH:20][N:19]2[N:22]=[CH:23][C:24]([NH:25][C:26]([N:28]3[CH2:31][C:30]([OH:33])([CH3:32])[CH2:29]3)=[O:27])=[C:18]2[N:17]=1.[ClH:34]>O1CCOCC1>[ClH:34].[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]1[CH:21]=[CH:20][N:19]2[N:22]=[CH:23][C:24]([NH:25][C:26]([N:28]3[CH2:31][C:30]([OH:33])([CH3:32])[CH2:29]3)=[O:27])=[C:18]2[N:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 58386280HCID 58386280, compound

Product 1

HCID 67307280(R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxy-3-methylazetidine-1-carboxamide hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a methanol (1 mL) solution of (R)—N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxy-3-methylazetidine-1-carboxamide (10.2 mg, 0.0238 mmol) was added HCl as a solution is dioxane (30 μL). After 30 minutes, the reaction was concentrated to provide (R)—N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxy-3-methylazetidine-1-carboxamide hydrochloride (8.3 mg, 0.0179 mmol, 75.0% yield) as a yellow solid.

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-ae239751b473426d8cb24e7dd7da596e
Source dataset
uspto-grants-2016_01
Patent number
US09227975B2

Reaction notes

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