Triethylamine → HCID 45275878, compound

HRID 1622388Notes

Reaction equation

HRID 1622388 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1Cl.[C:10]([NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:12])[CH3:11].C(N(CC)CC)C>CN1C(=O)CCC1>[Cl:9][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[N:17]1[CH2:18][CH2:19][CH:14]([NH:13][C:10](=[O:12])[CH3:11])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14451564-AcetamidopiperidineHCID 37865313,4,5-Trichloropyridine

Product 1

HCID 45275878HCID 45275878, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

General procedure C was followed using 3,4,5-trichloropyridine (50 mg, 0.27 mmol), 4-acetamidopiperidine (43 mg, 0.30 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, MeOH, 1:1:0.05) to furnish the title compound as white solid (7 mg, 9%), LC-MS (ESI, 3.5 min) Rt 2.25 min; m/z (ESI) C12H16Cl2N3O requires 288.0665 found [M+H]+ 288.0664; HPLC Rt 5.98 min, 100%.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (hexane, EtOAc, MeOH, 1:1:0.05)

Sources & evidence

ORD record
ord-fe6180f02242400d81662417b437085e
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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