Trifluoroacetic acid → HCID 67377029, compound

HRID 522874Notes

Reaction equation

HRID 522874 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH:13]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[C:9]([C:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH:13]=3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67376805HCID 67376805, compound

Product 1

HCID 67377029HCID 67377029, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-phenylthiazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (206 mg, 0.602 mmol) in CH2Cl2 (2.4 mL) was added TFA (0.232 mL). The solution turned bright red immediately, and after stirring overnight the color had become orange. The solution was concentrated under reduced pressure and the crude oil obtained purified with a 5 g SCX-2 column washing first with MeOH, then with 2M NH3 in MeOH leading to elution of basic materials. Upon drying, 4-phenyl-2-(1,2,3,6-tetrahydropyridin-4-yl)thiazole (121 mg, 0.499 mmol, 83%) was obtained as a yellow oil.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe crude oil obtained
  3. custompurified with a 5 g SCX-2 column
  4. washwashing first with MeOH
  5. washwith 2M NH3 in MeOH leading to elution of basic materials
  6. customUpon drying

Sources & evidence

ORD record
ord-a46952dc646441549d324dd13eab4f6a
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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