Trifluoroacetic acid → Methyl 5-(2-aminoethoxy)-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate

HRID 577585Notes

Reaction equation

HRID 577585 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([C:23]([O:25][CH3:26])=[O:24])=[C:14]([CH3:22])[C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[N:16][CH:17]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([C:23]([O:25][CH3:26])=[O:24])=[C:14]([CH3:22])[C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86723811Methyl 5-{2-[(tert-butoxycarbonyl)amino]ethoxy}-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate

Product 1

HCID 86723813Methyl 5-(2-aminoethoxy)-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylateYield 260.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-{2-[(tert-butoxycarbonyl)amino]ethoxy}-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate (131d, 0.74 g, 2.0 mmol) in dry CH2Cl2 (20 mL) was added TFA (5 mL) at 5° C. The mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under vacuum to give methyl 5-(2-aminoethoxy)-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate (131e, 1.4 g) as brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-4889134a02f141f0ac18f1d736eec5fc
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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