Trifluoroacetic acid → HCID 59177778, compound

HRID 423650Notes

Reaction equation

HRID 423650 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][C:14]([O:17][CH:18]([CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29](C)([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)[CH3:19])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O.C(N(C(C)C)CC)(C)C.ClC(OC(C)C)=O>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][C:14]([O:17][CH:18]([CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)[CH3:19])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 59177742(+/-)-1,1-Dimethylethyl 4-[1-({5-[4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)ethyl]-1-piperidinecarboxylate

Product 1

HCID 59177778HCID 59177778, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (0.21 g, 98%) was prepared as a white foam from (±)-1,1-dimethylethyl 4-[1-({5-[4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)ethyl]-1-piperidinecarboxylate (Example 160, 0.22 g, 0.48 mmol) and TFA (0.37 mL) in CH2Cl2 (16 mL) then diisopropylethylamine (1.25 mL) and isopropyl chloroformate (1.0M in toluene, 0.57 mL, 0.57 mmol) in a manner similar to Example 74. The crude material was purified by chromatography on a silica gel column eluted with 50% EtOAc/hexanes to afford (±)-1-methylethyl 4-[1-({5-[4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)ethyl]-1-piperidinecarboxylate as a white foam. 1H NMR (400 MHz, CDCl3): δ 8.53 (d, 1H, J=1.0 Hz), 8.24 (d, 1H, J=1.2 Hz), 8.10 (d, 2H, J=8.5 Hz), 8.02 (d, 2H, J=8.6 Hz), 5.15-5.05 (m, 1H), 4.89 (septet, 1H, J=6.3 Hz), 4.30-4.15 (m, 2H), 3.07 (s, 3H), 2.75-2.65 (m, 2H), 1.85-1.65 (m, 3H), 1.40-1.25 (m, 5H), 1.22 (d, 6H, J=6.3 Hz); LRMS (ESI), m/z 448 (M+H).

Workup

  1. customThe crude material was purified by chromatography on a silica gel column
  2. washeluted with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-4d3e6ec0f4144e4f9d7f8b7ab5140fe4
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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