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

HRID 1640420노트

반응식

HRID 1640420 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7e08cca4e45e4fb18ba2e800e945a758
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114866B2

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