Cesium carbonate → 4-[(3-Chloro-pyrazin-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1351578노트

반응식

HRID 1351578 반응식
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][NH2:23])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][C:2]2[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 785752,3-DichloropyrazineHCID 7368171-Boc-4-(aminomethyl)piperidine

생성물 1

HCID 235773104-[(3-Chloro-pyrazin-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2,3-Dichloropyrazine (1.0 g, 0.0067 mol), tert-butyl-4-(aminomethyl)-piperidine-1-carboxylate (1.6 g, 0.0075 mol) (Astatech) and cesium carbonate (2.4 g, 0.0075 mol) in acetonitrile (10 mL)were heated to 90° C. under nitrogen for 18 h. The reaction was concentrated in vacuo, diluted with ethyl acetate (50 mL) and washed with water (50 mL). The organic extract was dried over sodium sulfate, filtered and chromatographed on silica using a gradient of 10 to 30% ethyl acetate/hexane to give the title compound as a foam. M.S. (M+1): 327

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with ethyl acetate (50 mL)
  3. washwashed with water (50 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. customchromatographed on silica using a gradient of 10 to 30% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-5a71e1e23c504d2a92f4f7ac3e644815
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217716B2

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