Triethylamine → HCID 45274905, compound

HRID 1622335Notes

Reaction equation

HRID 1622335 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:20])[C:18]=1Cl.C(N(CC)CC)C>CN1C(=O)CCC1>[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:20])[C:18]=1[N:8]1[CH2:7][CH2:6][CH:5]([C:3]([N:2]([CH3:11])[CH3:1])=[O:4])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 411689N,N-dimethylpiperidine-4-carboxamideHCID 37865313,4,5-Trichloropyridine

Product 1

HCID 45274905HCID 45274905, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

General procedure C was followed using N,N-dimethylpiperidine-4-carboxamide 6 (43 mg, 0.27 mmol), 3,4,5-trichloropyridine (50 mg, 0.27 mmol), triethylamine (76 μL, 0.54 mmol) and NMP (1.5 mL). The crude product was purified by flash column chromatography on silica gel (hexane/EtOAc, 1:1) to furnish the title compound as a white solid (66 mg, 80%), m.p. 120-122° C.; umax (CHCl3)/cm−1 3026, 2850, 1631, 1559, 1140, 1092, 934; m/z (ESI) C13H18Cl2N3O requires 302.0821, found [M+H]+ 302.0823.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-31e0e1d23af74a6c9f7d3d9d075b75c1
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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