Triethylamine → HCID 58378283, compound

HRID 1622328Notes

Reaction equation

HRID 1622328 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH2:10]2)=[O:8])[CH2:3][CH2:2]1.[Cl:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30]([Cl:33])[C:31]=1Cl.C(N(CC)CC)C>CN1C(=O)CCC1>[CH2:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][N:9]([C:7]([CH:4]2[CH2:5][CH2:6][N:1]([C:31]3[C:30]([Cl:33])=[CH:29][N:28]=[CH:27][C:26]=3[Cl:25])[CH2:2][CH2:3]2)=[O:8])[CH2:14][CH2:13]1)=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37865313,4,5-TrichloropyridineHCID 58378278HCID 58378278, compound

Product 1

HCID 58378283HCID 58378283, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

General procedure C (See Example 1) was followed using benzyl-4-(piperidine-4-carbonyl)piperazine-1-carboxylate 12 (0.11 g, 0.33 mmol), 3,4,5-trichloropyridine (61 mg, 0.33 mmol), NMP (2.5 mL) and triethylamine (93 μL, 0.66 mmol). The crude product was purified by flash column chromatography on silica gel (hexane, EtOAc, 1:1) to furnish the title compound 13 as a white solid (58 mg, 36%), umax (CHCl3)/cm−1 3023, 1699, 1635, 1559, 1432, 1285, 1232, 1015; m/z (ESI) C23H27Cl2N4O3 requires 477.1455, found [M+H]+ 477.1457.

Workup

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

Sources & evidence

ORD record
ord-efc77e3f979846b7b593c02620fa99e4
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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