Hydrochloric Acid → HCID 67342842, compound

HRID 451456Notes

Reaction equation

HRID 451456 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH:18][CH:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1.Cl>O1CCCC1.CO>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67342045HCID 67342045, compound

Product 1

HCID 67342842HCID 67342842, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-(8-(2-chloro-4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)piperidine-1-carboxylate (810 mg, 1.82 mmol) in tetrahydrofuran (8 mL) and methanol (6 mL) was added hydrogen chloride solution (4.0 M in dioxane, 2.3 mL, 9.1 mmol). The reaction mixture was stirred for 1.5 hours at 60° C. and then concentrated in vacuo. The residue was diluted with ethyl acetate (40 mL) and washed with aqueous sodium carbonate (1 M, 30 mL), water (30 mL) and brine (30 mL). The aqueous layers were extracted with further ethyl acetate (40 mL). The organic layers were combined, dried over magnesium sulfate and filtered off. Concentration afforded the title compound as yellow foam (639 mg, 98%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate (40 mL)
  3. washwashed with aqueous sodium carbonate (1 M, 30 mL), water (30 mL) and brine (30 mL)
  4. extractionThe aqueous layers were extracted with further ethyl acetate (40 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered off
  7. concentrationConcentration

Sources & evidence

ORD record
ord-174df197d3b2434399e20bbf2f91a65d
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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