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

HRID 1827216노트

반응식

HRID 1827216 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-65001163c56d4a838edbac600d091df5
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053089B2

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