Cesium carbonate → benzyl ((1S,3R)-3-(pyrazin-2-ylamino)cyclohexyl)carbamate

HRID 75051

반응식

HRID 75051 반응식
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].I[C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1.CC(C)C(C1CCCCC1=O)=O.C(=O)(O)[O-].[Na+]>CN(C=O)C.[Cu]I.C(OCC)(=O)C>[N:27]1[CH:28]=[CH:29][N:30]=[CH:31][C:26]=1[NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1

참가 물질

9

반응물 5

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 642841IodopyrazineHCID 114693012-(2-Methylpropanoyl)cyclohexan-1-oneHCID 69756715Benzyl ((1S,3R)-3-aminocyclohexyl)carbamate2회

생성물 1

HCID 68007319benzyl ((1S,3R)-3-(pyrazin-2-ylamino)cyclohexyl)carbamate

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of CuI (0.006 g, 0.030 mmol), benzyl N-[(1S,3R)-3-aminocyclo-hexyl]carbamate, 18e, (0.075 g, 0.302 mmol) and cesium carbonate (0.197 g, 0.604 mmol) in DMF was evacuated and refilled with nitrogen multiple times. 2-iodopyrazine (0.036 mL, 0.362 mmol) and 2-(2-methylpropanoyl)cyclohexanone (0.020 mL g, 0.121 mmol) were then added and the reaction was stirred at room temperature overnight. The reaction was diluted into ethyl acetate and aqueous saturated sodium bicarbonate. The organic phase was separated, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to afford 40 mg of the desired product as yellow solid.

후처리

  1. customwas evacuated
  2. additionrefilled with nitrogen multiple times
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-9b84f14b8bf940c9bf556156b1b98b6d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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