4-Piperidinecarboxamide → HCID 45275245, compound

HRID 1622353Notes

Reaction equation

HRID 1622353 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1Cl.[NH:10]1[CH2:18][CH2:17][CH:13]([C:14]([NH2:16])=[O:15])[CH2:12][CH2:11]1.C(N(CC)CC)C>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1[N:10]1[CH2:18][CH2:17][CH:13]([C:14]([NH2:16])=[O:15])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 8471TriethylamineHCID 8170943,5-Dibromo-4-chloropyridine

Product 1

HCID 45275245HCID 45275245, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

General procedure C was followed using 3,5-dibromo-4-chloropyridine 18 (50 mg, 0.18 mmol), isonipecotamide (24 mg, 0.18 mmol), NMP (2 mL) and triethylamine (51 μL, 0.37 mmol). The crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 9:1) to furnish the title compound as a pale yellow solid (29 mg, 43%), m.p. 158-160° C.; umax (CHCl3)/cm−1 3053, 2985, 1687, 1591; m/z (ESI) C11H14Br2N3O requires 361.9498 found [M+H]+ 361.9500.

Workup

  1. customThe crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 9:1)

Sources & evidence

ORD record
ord-d6e32d01eae44c9592f6b8f146c75367
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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