Pyridine → 2,2-dimethyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide

HRID 40538노트

반응식

HRID 40538 반응식
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>ClCCl>[CH3:24][C:23]([CH3:26])([CH3:25])[C:22]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][N:13]=1)=[O:27]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 468541905-Phenylethynyl-pyridin-2-ylamine

생성물 1

HCID 715482442,2-dimethyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide수율 43.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(65 mg, 0.33 mmol) 5-Phenylethynyl-pyridin-2-ylamine (Example 1, step 1) was dissolved in dichloromethane (3 ml). Pyridine (52 mg, 53 μl, 0.67 mmol, 2 equiv.) and pivaloyl chloride (48 mg, 50 μl, 0.40 mmol, 1.2 equiv.) were added and the mixture was stirred for 2 hours at room temperature. The reaction mixture was extracted with 1N HCl solution and twice with dichloromethane. The organic extracts were combined, dried over sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with heptane:dichloromethane 50:50. The desired 2,2-dimethyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide (40 mg, 43% yield) was obtained as a light yellow solid, MS: m/e=279.3 (M+H+).

후처리

  1. extractionThe reaction mixture was extracted with 1N HCl solution and twice with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by flash chromatography on a silica gel column
  5. washeluting with heptane:dichloromethane 50:50

출처 및 근거

ORD 기록
ord-f7268b02a0e74b34b0bacc1c837740c9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530472B2

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