Sulfuric Acid → (R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxyazetidine-1-carboxamide sulfate

HRID 537756

Reaction equation

HRID 537756 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([NH:23][C:24]([N:26]3[CH2:29][CH:28]([OH:30])[CH2:27]3)=[O:25])=[C:16]2[N:15]=1.[S:31](=[O:35])(=[O:34])([OH:33])[OH:32]>CO>[S:31]([OH:35])([OH:34])(=[O:33])=[O:32].[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([NH:23][C:24]([N:26]3[CH2:29][CH:28]([OH:30])[CH2:27]3)=[O:25])=[C:16]2[N:15]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 46188750(R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxyazetidine-1-carboxamide

Product 1

HCID 67330348(R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxyazetidine-1-carboxamide sulfateYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (R)—N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxyazetidine-1-carboxamide (44 mg, 0.11 mmol) in methanol (3 mL) at ambient temperature was added sulfuric acid in methanol (531 μL, 0.11 mmol). The resulting solution was stirred for 30 minutes then concentrated to provide (R)—N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxyazetidine-1-carboxamide sulfate (38 mg, 0.074 mmol, 70% yield) as a yellow solid.

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-f286e857d9df43529659b987f7a24bc1
Source dataset
uspto-grants-2014_10
Patent number
US08865698B2

Linked notes

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