HCID 58728486, compound → HCID 58961066, compound

HRID 1992070Notes

Reaction equation

HRID 1992070 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[O:10][N:9]=2)[CH:2]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:16]1[CH2:15][CH2:14][CH:13]([C:11]2[O:10][N:9]=[C:8]([CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[N:12]=2)[CH2:18][CH2:17]1

Participants

3

Reactant 1

HCID 58728486HCID 58728486, compound

Product 1

HCID 58961066HCID 58961066, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-Butyl 4-[3-(pyridin-3-ylmethyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate was treated with 10 mL TFA/DCM (1:1) for 30 min at ambient temperature. The reaction mixture was concentrated to give the di-TFA salt of 3-[(5-piperidin-4-yl-1,2,4-oxadiazol-3-yl)methyl]pyridine as an amber oil (4.0 g, 8.47 mmol, 85%, 3 steps). 1H NMR (300 MHz, DMSO-d6) δ 8.78 (s, 1H), 8.70 (d, 1H, J=5.0 Hz), 8.51 (br.s, 1H), 8.18 (d, 1H, J=7.9 Hz), 7.75 (m, 1H), 4.30 (s, 2H), 3.44-3.30 (m, 3H), 3.09-3.00 (m, 2H), 2.20-2.16 (m, 2H), 1.93-1.80 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-e9d44472885443acb0d8dae97b2e34ba
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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