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Hydrochloric Acid → N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine dihydrochloride

HRID 473709
Notes
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Reaction equation

HRID 473709 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:33]=[CH:32][C:11]([O:12][C:13]2[C:14]([C:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH:20]=3)=[N:15][CH:16]=[CH:17][N:18]=2)=[CH:10][CH:9]=1.C(Cl)[Cl:35].[ClH:37]>O1CCOCC1>[ClH:35].[ClH:37].[NH:22]1[CH2:21][CH2:20][CH:19]([C:14]2[C:13]([O:12][C:11]3[CH:32]=[CH:33][C:8]([NH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[CH:9][CH:10]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:24][CH2:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 6344DichloromethaneHCID 59374036tert-butyl 4-(3-(4-(pyridin-2-ylamino)phenoxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 67425394N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine dihydrochloride

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent
2×

Procedure

To a solution of tert-butyl 4-(3-(4-(pyridin-2-ylamino)phenoxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (5.2 g, 11.67 mmol) and DCM (100 mL) was added 4M HCl in dioxane (12 mL, 48.0 mmol). After 4 hours, another 5 mL of 4M HCl in dioxane was added. After a further 16 hours, the precipitates had clung to the walls of the flask and the clear stirring solution was decanted away. The precipitates were washed with another 50 mL of DCM and the solution again decanted away. The flask was placed under vacuum for 30 minutes to give N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine dihydrochloride as a hydroscopic yellow solid.

Workup

  1. waitAfter a further 16 hours
  2. customthe clear stirring solution was decanted away
  3. washThe precipitates were washed with another 50 mL of DCM
  4. customthe solution again decanted away
  5. waitThe flask was placed under vacuum for 30 minutes

Sources & evidence

ORD record
ord-e10ea50882b549f3973317976f9f5d2f
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637500B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes