Trifluoroacetic acid → HCID 59177760, compound

HRID 423639Notes

Reaction equation

HRID 423639 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25](OC(C)(C)C)=O)[CH2:21][CH2:20]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+].ClC1[CH:51]=[CH:50][C:49]([C:52]([F:55])([F:54])[F:53])=[CH:48][N:47]=1>C(Cl)Cl.CS(C)=O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:51]=[CH:50][C:49]([C:52]([F:55])([F:54])[F:53])=[CH:48][N:47]=4)[CH2:21][CH2:20]3)=[CH:15][N:16]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 249943331,1-Dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate

Product 1

HCID 59177760HCID 59177760, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound (73 mg, 66%) was prepared as a white solid from 1,1-dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (prepared as in Example 150, Step 2, 0.10 g, 0.22 mmol) and TFA (0.18 mL) in CH2Cl2 (6 mL) then K2CO3 (0.62 g) and 2-chloro-5-(trifluoromethyl)pyridine (50 mg, 0.27 mmol) in DMSO (5 mL) in a manner similar to Example 80. The crude material was purified by chromatography on a silica gel column eluted with 1:16 acetone/CH2Cl2 to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.40 (d, 1H, J=2.9 Hz), 8.36 (s, 1H), 8.24 (d, 2H, J=8.3 Hz), 8.02 (d, 1H, J=8.8 Hz), 7.95 (d, 2H, J=8.3 Hz), 7.75-7.70 (m, 1H), 7.51 (dd, 1H, Ja=8.8 Hz, Jb=3.0 Hz), 6.94 (d, 1H, J=9.1 Hz), 4.50-4.40 (m, 2H), 3.99 (d, 2H, J=6.4 Hz), 3.21 (s, 3H), 3.00-2.90 (m, 2H), 2.20-2.05 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 492 (M+H).

Workup

  1. customThe crude material was purified by chromatography on a silica gel column
  2. washeluted with 1:16 acetone/CH2Cl2

Sources & evidence

ORD record
ord-397b1740088c476da532d390a2d01bec
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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