Water → 2-(Methylamino)-2-oxoethyl 4-[6-(2-methylpropyl)-3-pyridyl]-1-piperazinecarboxylate

HRID 1640420Notes

Reaction equation

HRID 1640420 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]([NH:20][CH3:21])=[O:19])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[Zn][CH2:24][CH:25]([CH3:27])[CH3:26].O.C(OCC)(=O)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:24][CH:25]([CH3:27])[CH2:26][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]([NH:20][CH3:21])=[O:19])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 602095632-(Methylamino)-2-oxoethyl 4-(6-bromo-3-pyridyl)-1-piperazinecarboxylateHCID 178448255HCID 178448255, compound

Product 1

HCID 592182212-(Methylamino)-2-oxoethyl 4-[6-(2-methylpropyl)-3-pyridyl]-1-piperazinecarboxylate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

1.25 g (3.50 mmol) of 2-(methylamino)-2-oxoethyl 4-(6-bromo-3-pyridyl)-1-piperazinecarboxylate, prepared in step 9.1, and 0.12 g (0.17 mmol) of dichlorobis(triphenylphosphine)palladium (Pd(PPh3)2Cl2) suspended in 7 ml of tetrahydrofuran are introduced under an inert atmosphere. 17.50 ml (8.74 mmol) of a solution of bromoisobutylzinc (0.5M) in tetrahydrofuran are then added. Stirring is continued at room temperature for 19 hours. The reaction mixture is poured into 25 ml of water and 25 ml of ethyl acetate. The insoluble material is filtered off through glass fiber. The phases are separated by settling, the aqueous phase is extracted twice with ethyl acetate, the combined organic phases are dried over sodium sulfate and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by chromatography on silica gel, eluting with a 95/5 mixture of dichloromethane and methanol, followed by crystallization from diisopropyl ether. 0.36 g of product is obtained in the form of a brown solid.

Workup

  1. additionare introduced under an inert atmosphere
  2. filtrationThe insoluble material is filtered off through glass fiber
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases are dried over sodium sulfate
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue thus obtained
  8. customis purified by chromatography on silica gel
  9. washeluting with a 95/5 mixture of dichloromethane and methanol
  10. customfollowed by crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-7e08cca4e45e4fb18ba2e800e945a758
Source dataset
uspto-grants-2012_02
Patent number
US08114866B2

Reaction notes

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