Trifluoroacetic acid → HCID 66876080, compound

HRID 1666502Notes

Reaction equation

HRID 1666502 reaction equation
[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:12][C:13]3[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=3)[CH:16]=[C:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)=[N:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:20]1[CH2:21][CH2:22][C:17](=[CH:16][C:15]2[CH:14]=[C:13]([CH:32]=[CH:31][CH:30]=2)[O:12][C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:11][N:10]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66875895HCID 66875895, compound

Product 1

HCID 66876080HCID 66876080, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-(5-(pyrrolidin-1-yl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.335 g, 0.769 mmol) in CH2Cl2 (5 mL) cooled to 0° C. under a N2 atmosphere was added TFA (0.88 mL, 11.49 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 (0.224 g, 86.8%). 1H NMR (500 MHz, DMSO-d6): δ 7.59 (s, 1H), 7.23 (m, 1H), 6.95 (m, 1H), 6.89 (d, J=7.5 Hz, 1H), 6.82 (m, 3H), 6.25 (s, 1H), 3.27 (m, 4H), 2.98 (m, 2H), 2.86 (m, 2H), 2.49 (m, 2H), 2.34 (m, 2H), 2.02 (m, 4H); m/z (336.2, MH+).

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-39b8b043b729419cb8260f3027d68d37
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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