Hydrochloride methanol → 2-(3-((5-(Piperidin-4-yl)pyrimidin-4-yl)oxy)azetidin-1-yl)quinoline hydrochloride

HRID 2207843Notes

Reaction equation

HRID 2207843 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([O:15][C:16]2[C:21]([CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[CH:20][N:19]=[CH:18][N:17]=2)[CH2:12]1.[ClH:35].CO>>[ClH:35].[NH:25]1[CH2:26][CH2:27][CH:22]([C:21]2[C:16]([O:15][CH:13]3[CH2:12][N:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)[CH2:14]3)=[N:17][CH:18]=[N:19][CH:20]=2)[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 58547690Tert-butyl 4-(4-((1-(quinolin-2-YL)azetidin-3-YL)oxy)pyrimidin-5-YL)piperidine-1-carboxylate

Product 1

HCID 674774162-(3-((5-(Piperidin-4-yl)pyrimidin-4-yl)oxy)azetidin-1-yl)quinoline hydrochloride

Procedure

The mixture of tert-butyl 4-(4-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrimidin-5-yl)piperidine-1-carboxylate (307 mg, 0.66 mmol) in HCl/MeOH (10 mL, saturated with HCl gas) was stirred at room temperature for 1 hour. Then it was concentrated to give 2-(3-((5-(piperidin-4-yl)pyrimidin-4-yl)oxy)azetidin-1-yl)quinoline hydrochloride which was used in the next step below without further purification.

Workup

  1. concentrationThen it was concentrated

Sources & evidence

ORD record
ord-479b4f31b7344ba499179969545e6ec2
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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