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Hydrochloric Acid → 2-(4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxylic acid

HRID 80668
Notes
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Reaction equation

HRID 80668 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:18]=[N:17][N:16]([CH:19]4[CH2:24][CH2:23][N:22]([C:25]5[N:30]=[CH:29][C:28]([C:31]([O-:33])=[O:32])=[CH:27][N:26]=5)[CH2:21][CH2:20]4)[N:15]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[OH-].[Na+].Cl>CO>[N:1]1([C:6]2[N:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:18]=[N:17][N:16]([CH:19]4[CH2:20][CH2:21][N:22]([C:25]5[N:26]=[CH:27][C:28]([C:31]([OH:33])=[O:32])=[CH:29][N:30]=5)[CH2:23][CH2:24]4)[N:15]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866306322-(4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxylate

Product 1

HCID 577083752-(4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-(2-(4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxylate (0.8 g, 0.00167 mol) (Example 60) was dissolved in MeOH (20 mL). An aqueous solution of NaOH (10 eq., 40 mL) was added and the reaction mixture was heated at 60° C. for three hours. The methanol was removed in vacuo and the remaining reaction mixture was cooled to 0° C. and concentrated HCl was added drop wise until the pH reached 2-3. The aqueous solution was extracted with DCM, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound.

Workup

  1. customThe methanol was removed in vacuo
  2. customthe remaining reaction mixture
  3. temperaturewas cooled to 0° C.
  4. extractionThe aqueous solution was extracted with DCM
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a97014e229f467b97880a94e9d77c06
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846675B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes