HCID 58993469, compound → HCID 58993573, compound

HRID 391477Notes

Reaction equation

HRID 391477 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([C@H:19]([O:21][CH2:22][C:23]3([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)[CH3:20])[CH:10]=2)=[CH:5][CH:4]=1)#[N:2]>FC(F)(F)C(O)=O>[C:36]1([C:23]2([CH2:22][O:21][C@@H:19]([C:11]3[CH:10]=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=4)[CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:12]=3)[CH3:20])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 1

HCID 58993469HCID 58993469, compound

Product 1

HCID 58993573HCID 58993573, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-tert-Butyl 4-((1-(4′-cyano-5-(trifluoromethyl)biphenyl-3-yl)ethoxy)methyl)-4-phenylpiperidine-1-carboxylate (10 mg, 0.018 mmol) was dissolved in trifluoroacetic acid (33% in dichloromethane, 1.5 mL). The resulting solution was stirred at room temperature for 1 h and concentrated. The crude salt was loaded onto an SCX cartridge in methanol. The cartridge was flushed with several volumes of methanol which was discarded. The product was eluted with 2 M ammonia in methanol and concentrated to give 7.2 mg (88%) as a colorless film. 1H NMR (500 MHz, CDCl3) δ ppm 7.73 (d, J=8.6 Hz, 2H), 7.64 (s, 1H), 7.55 (d, J=8.6 Hz, 2H), 7.38 (s, 2H), 7.20-7.35 (m, 4H), 7.16 (m, 1H), 4.29 (q, J=6.4 Hz, 1H), 3.46 (s, 1H), 3.33 (d, J=9.2 Hz, 1H), 3.25 (d, J=8.9 Hz, 1H), 2.90 (m, 2H), 2.73 (m, 2H), 2.00-2.25 (m, 2H), 1.80-1.99 (m, 2H), 1.35 (d, J=6.4 Hz, 3H). Mass spec.: 465.20 (MH)+. Accurate mass spec.: m/z 465.2136 [MH]+, Δ=3.8 ppm.

Workup

  1. concentrationconcentrated
  2. customThe cartridge was flushed with several volumes of methanol which
  3. washThe product was eluted with 2 M ammonia in methanol
  4. concentrationconcentrated
  5. customto give 7.2 mg (88%) as a colorless film

Sources & evidence

ORD record
ord-2de8cb308d9e452a83a4b5b8cb961d30
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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