Trifluoroacetic acid → (4-(Azetidin-3-yl)piperazin-1-yl)(thiazol-2-yl)methanone

HRID 2365284Notes

Reaction equation

HRID 2365284 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[S:21][CH:22]=[CH:23][N:24]=3)=[O:19])[CH2:14][CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]([C:20]3[S:21][CH:22]=[CH:23][N:24]=3)=[O:19])[CH2:16][CH2:17]2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596260133-[4-(Thiazole-2-carbonyl)-piperazin-1-yl]-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59625677(4-(Azetidin-3-yl)piperazin-1-yl)(thiazol-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 7c (1.2 g, 3.41 mmol) in CH2Cl2 (12 mL) was added TFA (3 mL). The reaction mixture was stirred at room temperature for 4.5 h, concentrated, and to the resulting residue was added aq. NaHCO3. The mixture was extracted with 2% MeOH/CH2Cl2 (3×). The organic solution was dried over Na2SO4 and concentrated to give compound 5e, which was used in the next reaction without further purification.

Workup

  1. concentrationconcentrated
  2. additionto the resulting residue was added aq. NaHCO3
  3. extractionThe mixture was extracted with 2% MeOH/CH2Cl2 (3×)
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1dadb92a51494e438ae249ce7f911a03
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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