Trifluoroacetic acid → HCID 66876070, compound

HRID 1666419Notes

Reaction equation

HRID 1666419 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=2)[CH:15]=[C:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[N:9][CH:10]=1)([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:31]=[CH:30][CH:29]=[C:14]([CH:15]=[C:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[CH:13]=2)=[N:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66876886HCID 66876886, compound

Product 1

HCID 66876070HCID 66876070, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-(5-isopropoxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.5 g, 1.17 mmol) in CH2Cl2 (3 mL) cooled to 0° C. under a N2 atmosphere was added TFA (0.46 mL, 5.97 mmol). The resulting mixture was stirred for 2 h at RT. The solution was concentrated and then quenched with saturated NaHCO3 solution. The mixture was extracted with CH2Cl2 and the organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (0.38 g, 99%). 1H NMR (500 MHz, CDCl3): δ 8.94 (m, 2H), 7.35 (m, 2H), 7.0 (m, 2H), 6.90 (s, 1H), 6.47 (s, 1H), 4.53 (m, 1H), 3.50 (m, 2H), 3.32 (m, 2H), 2.76 (m, 2H), 2.65 (m, 2H), 1.35 (d, J=6 Hz, 6H).

Workup

  1. concentrationThe solution was concentrated
  2. customquenched with saturated NaHCO3 solution
  3. extractionThe mixture was extracted with CH2Cl2
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-906050cc5a294c36b324c906e12d0c50
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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