Hydrochloric Acid → 2-Morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-amine

HRID 588433

Reaction equation

HRID 588433 reaction equation
[N:1]1([C:7]2[N:23]=[C:10]3[CH:11]=[CH:12][C:13]([NH:15]C(=O)OC(C)(C)C)=[CH:14][N:9]3[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl>>[N:1]1([C:7]2[N:23]=[C:10]3[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][N:9]3[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 89464434Tert-butyl 2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamate

Product 1

HCID 894644042-Morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-amineYield 91%

Conditions

Temperature
25 °C

Procedure

A mixture of tert-butyl 2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamate (363 mg, 1.14 mmol) and hydrochloric acid (5M in diethyl ether, 24.0 g, 20 ml, 100 mmol) was stirred for 5 hours at 25° C. and then the solvent was evaporated under reduced pressure. The light yellow residue was made alkaline using sodium hydroxide solution (2 M in water). The mixture was extracted 2 times with ethyl acetate, the organic layers were combined, washed with water and brine, dried over magnesium sulfate, filtrated and evaporated to dryness, affording 2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylamine (227 mg, 91%) as grey solid. Mp.: 165° C. MS: m/z=220.1 (M+H+).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. extractionThe mixture was extracted 2 times with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0cf881196d4f4b60a456c2cf0f2855fb
Source dataset
uspto-grants-2016_01
Patent number
US09227970B2

Linked notes

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