Hydrochloric Acid → (R)-N-(2-hydroxyethyl)-3-(pyrrolidin-2-ylmethoxy)picolinamide dihydrochloride

HRID 2406793Notes

Reaction equation

HRID 2406793 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:12]([O:13][CH2:14][C@H:15]2[CH2:19][CH2:18][CH2:17][N:16]2C(OC(C)(C)C)=O)=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].[ClH:27]>CO>[ClH:27].[ClH:27].[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[C:7]1[C:12]([O:13][CH2:14][C@H:15]2[CH2:19][CH2:18][CH2:17][NH:16]2)=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66961789(R)-tert-butyl 2-((2-(2-hydroxyethylcarbamoyl)pyridin-3-yloxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 66962029(R)-N-(2-hydroxyethyl)-3-(pyrrolidin-2-ylmethoxy)picolinamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-tert-butyl 2-((2-(2-Hydroxyethylcarbamoyl)Pyridin-3-Yloxy)Methyl)Pyrrolidine-1-Carboxylate (330 mg, 0.90 mmol, EXAMPLE 33 Step 3) was dissolved in 10% hydrogen chloride in methanol (8 mL) at room temperature. After being stirred at room temperature for 4 days, the volatile was evaporated to afford 304 mg (quant.) of the title compound that was used directly in the next step without further purification.

Workup

  1. customthe volatile was evaporated

Sources & evidence

ORD record
ord-4579f4b738d64954bd3cd878cf03a98e
Source dataset
uspto-grants-2014_08
Patent number
US08809380B2

Reaction notes

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