Potassium Carbonate → Methyl 5-{4-[(1-cyclobutyl-4-piperidinyl)methyl]-1-piperidinyl}-2-pyrazinecarboxylate

HRID 1869633Notes

Reaction equation

[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([CH2:11][CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.Cl[C:19]1[N:20]=[CH:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[N:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([CH2:11][CH:12]3[CH2:17][CH2:16][N:15]([C:19]4[N:20]=[CH:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[N:23][CH:24]=4)[CH2:14][CH2:13]3)[CH2:9][CH2:10]2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

1-Cyclobutyl-4-(4-piperidinylmethyl)piperidine (may be prepared as described in Description 6) (0.59 g), methyl 5-chloro-2-pyrazinecarboxylate (0.43 g) and potassium carbonate (0.69 g) were dissolved in acetonitrile (5 ml) and heated at 120° C. for 10 min in the microwave reactor, followed by a further 15 min. The crude mixture was passed through an SCX column (10 g, eluting with methanol [80 ml] then 2 N NH3 in methanol [80 ml]). The basic fractions were evaporated to give the title compound (E1) as a yellow solid (0.665 g). MS electrospray (+ion) 373 (MH+)

Workup

washeluting with methanol [80 ml]
customThe basic fractions were evaporated

Sources & evidence

ORD record: ord-a87dcd2bcb9b4e3da630a7a4f659135c
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638631B2

Reaction notes

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