Ethanol → (4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethylpyrazin-2-yl)-methanone

HRID 551595Notes

Reaction equation

HRID 551595 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([CH:11]=[O:12])=[CH:7][N:6]=1)=O.COC([C:17]1[CH:22]=[N:21][C:20](C(Br)Br)=[CH:19][N:18]=1)=O.[CH2:26](O)[CH3:27]>C1COCC1.O.[N+]([O-])([O-])=O.[Ag+]>[CH:5]([N:18]1[CH2:17][CH2:22][N:21]([C:11]([C:8]2[CH:7]=[N:6][C:5]([CH2:3][N:6]3[CH2:27][CH2:26][CH2:11][CH2:8][CH2:7]3)=[CH:10][N:9]=2)=[O:12])[CH2:20][CH2:19]1)([CH3:10])[CH3:3]

Participants

7

Reactant 3

HCID 702EthanolHCID 44515461Methyl 5-formylpyrazine-2-carboxylateHCID 67188344Methyl 5-(dibromomethyl)pyrazine-2-carboxylate

Product 1

HCID 11544498(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethylpyrazin-2-yl)-methanone

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

5-Formyl-pyrazine-2-carboxylic acid methyl ester. A solution of 5-dibromomethyl-pyrazine-2-carboxylic acid methyl ester (1.00 g, 3.23 mmol) in a mixture of ethanol (20 mL) and THF (10 mL) was heated to 80° C. A solution of silver nitrate (2.20 g, 12.9 mmol) in H2O (4 mL) was added. The reaction mixture was heated at 80° C. for 1.25 h and was filtered while hot. The filtrate was concentrated to yield the title compound (1.36 g). This material was carried to the next step without purification.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 1.25 h
  2. filtrationwas filtered while hot
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-de9ce484df8e400fb0a67418e154f2f9
Source dataset
uspto-grants-2011_05
Patent number
US07947718B2

Reaction notes

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