1,4-Dioxane hydrochloride → N-(3-methylpyridin-2-yl)-N-[(3R)-piperidin-3-yl]-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamide hydrochloride

HRID 588388Notes

Reaction equation

HRID 588388 reaction equation
[CH3:1][C:2]1[C:3]([N:8]([C@@H:26]2[CH2:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]2)[C:9](=[O:25])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[ClH:39].O1CCOCC1>O1CCOCC1>[ClH:39].[CH3:1][C:2]1[C:3]([N:8]([C@@H:26]2[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]2)[C:9](=[O:25])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 117652897(R)-tert-butyl 3-(N-(3-methylpyridin-2-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)piperidine-1-carboxylate2×

Product 1

HCID 117652786N-(3-methylpyridin-2-yl)-N-[(3R)-piperidin-3-yl]-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound from Step 2 (R)-tert-butyl 3-(N-(3-methylpyridin-2-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)piperidine-1-carboxylate (737 mg, 1.44 mmol) in 1,4-dioxane (10 mL) was added HCl/1,4-dioxane (7.2 mL of 4 M, 28.8 mmol) dropwise at 0° C. The reaction was stirred at room temperature for 3 h. The resulting mixture was concentrated under reduced pressure. The crude product was purified by preparatory HPLC to deliver the hydrochloride salt of the title compound (325 mg, 52%) as a yellow solid

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customThe crude product was purified by preparatory HPLC

Sources & evidence

ORD record
ord-00157e2141d0416ab153753ad06a4e6c
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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