Trifluoroacetic acid → HCID 60019900, compound

HRID 1454818Notes

Reaction equation

HRID 1454818 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C:15](=[O:21])[N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[N:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C:8]1[N:9]=[C:10]([CH2:14][C:15]([N:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[O:21])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68843131HCID 68843131, compound

Product 1

HCID 60019900HCID 60019900, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

(6-Diethylcarbamoylmethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (0.2 g) in CH2Cl2 (10 mL) was treated at RT with trifluoro-acetic acid (0.5 mL) and the solution was stirred for 1.5 h until the reaction was complete according to the analysis. The mixture was allowed to warm to 10° C. and partitioned between aqueous diluted KHCO3 and AcOEt, the layers were separated, the organic layer dried over Na2SO4, filtered, evaporated to give 2-(6-amino-pyridin-2-yl)-N,N-diethyl-acetamide (148 mg) as a light yellow solid that was directly used in the next step.

Workup

  1. custompartitioned between aqueous diluted KHCO3 and AcOEt
  2. customthe layers were separated
  3. dry with materialthe organic layer dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9cc5d0d801d6474da3127745d2745c78
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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