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

HRID 869642Notes

Reaction equation

HRID 869642 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-2366f1b762c14dd3b2403ec4e2f0ec49
Source dataset
uspto-grants-2015_03
Patent number
US08969383B2

Reaction notes

Loading…