Triethylamine → HCID 45275018, compound

HRID 1622339Notes

Reaction equation

HRID 1622339 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([Cl:18])[C:16]=1Cl.C(N(CC)CC)C>CN1C(=O)CCC1>[Cl:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([Cl:18])[C:16]=1[N:7]1[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 837951-AcetylpiperazineHCID 37865313,4,5-Trichloropyridine

Product 1

HCID 45275018HCID 45275018, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

General procedure C was followed using acetylpiperazine (35 mg, 0.27 mmol), 3,4,5-trichloropyridine (50 mg, 0.27 mmol), triethylamine (0.76 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 (18 mg, 24%), m.p. 144-146° C.; umax (CHCl3)/cm−1 3008, 2909, 2856, 1638, 1558, 1470, 1441, 1282, 1240, 1152, 1098; m/z (ESI) C11H14Cl2N3O requires 274.0508, found [M+H]+ 274.0513.

Workup

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

Sources & evidence

ORD record
ord-20adedd5be9148338d47ef547f6f003d
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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