Trifluoroacetic acid → HCID 66876380, compound

HRID 1666506Notes

Reaction equation

HRID 1666506 reaction equation
[N:1]1([C:5]2[CH:6]=[CH:7][C:8]([O:11][C:12]3[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=3)[CH:15]=[C:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[N:9][CH:10]=2)[CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1([C:5]2[CH:6]=[CH:7][C:8]([O:11][C:12]3[CH:31]=[CH:30][CH:29]=[C:14]([CH:15]=[C:16]4[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]4)[CH:13]=3)=[N:9][CH:10]=2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66876064HCID 66876064, compound

Product 1

HCID 66876380HCID 66876380, compoundYield 952.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-(5-(azetidin-1-yl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.135 g, 0.32 mmol) in CH2Cl2 (5 mL) cooled to 0° C. under a N2 atmosphere was added TFA (0.24 mL, 3.2 mmol). The resulting mixture was stirred for 1 h at RT. The solution was concentrated and then quenched with saturated NaHCO3 solution. The mixture was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (0.98 g, 96%). 1H NMR (500 MHz, DMSO-d6): δ 7.46 (s, 1H), 7.28 (s, 1H), 6.91 (d, J=7.5 Hz, 1H), 6.85 (m, 4H), 6.28 (s, 1H), 3.87 (t, J=7 Hz, 4H), 3.02 (m, 2H), 2.90 (m, 2H), 2.53 (m, 2H), 2.39 (m, 4H).

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-ef445388d6504c7f908d025be59998d0
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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