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Toluene → 4-[(3-Methoxy-5-methyl-pyrazin-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1351587
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HRID 1351587 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([O:22][CH3:23])=[N:20][C:19](Br)=[CH:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][Zn]C.C1(C)C=CC=CC=1>O1CCCC1.O.C(OCC)(=O)C.[Ni](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([O:22][CH3:23])=[N:20][C:19]([CH3:25])=[CH:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

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반응물 3

HCID 1140TolueneHCID 235773094-[(5-Bromo-3-methoxy-pyrazin-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl esterHCID 178477796HCID 178477796, 화합물

생성물 1

HCID 235773064-[(3-Methoxy-5-methyl-pyrazin-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 4

HCID 2724937
Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickel
촉매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

실험 절차

To 4-[(5-bromo-3-methoxy-pyrazin-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (EXAMPLE 131, STEP 1) (0.20 g, 0.0005 mol) in tetrahydrofuran (1 mL), under nitrogen, was added 1,3-bis(diphenylphosphino)propane nickel(II) chloride (0.034 g, 0.0625 mmol) followed by a dropwise addition of 2.0M dimethylzinc in toluene (0.313 mL, 0.000625 mol). The reaction mixture was stirred for 1.5 h, diluted with water (5 mL) and ethyl acetate (30 mL). The organic layer was removed, dried over sodium sulfate, filtered and concentrated to an oil. The oil was chromatographed on silica using a gradient of 20–50% ethyl acetate/hexane to give the title compound as a foam. M.S. (M+1): 337.

후처리

  1. customThe organic layer was removed
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. customThe oil was chromatographed on silica using a gradient of 20–50% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-69440fd467414c57abc43f9364076490
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07217716B2

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