Trifluoroacetic acid → HCID 24825982, compound

HRID 910929Notes

Reaction equation

HRID 910929 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][CH:15]3[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]3)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 24825876HCID 24825876, compound

Product 1

HCID 24825982HCID 24825982, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100 mL round bottom flask was charged with tert-butyl 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)piperidine-1-carboxylate (1.65 g, 4.23 mmol) in dichloromethane (10 mL), and 2,2,2-trifluoroacetic acid (0.977 mL, 12.7 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. A saturated solution of NaHCO3 was added, and the solution was extracted with EtOAc and dichloromethane. The combined organic layers were filtered and concentrated to provide 4-methyl-N-(4-(piperidin-3-yloxy)pyridin-2-yl)thiazol-2-amine as a light yellow solid. (0.70 g, 53.6% yield). Mass spectrum (apci) m/z=291 (100) (+H).

Workup

  1. additionwas added
  2. extractionthe solution was extracted with EtOAc and dichloromethane
  3. filtrationThe combined organic layers were filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-69ac81a0964b44dab8497b34434a0c1e
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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