Water → N-[6-chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-yl]-butyramide

HRID 1043997

반응식

HRID 1043997 반응식
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:5]([NH2:14])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:21](Cl)(=[O:25])[CH2:22][CH2:23][CH3:24].O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]([CH3:11])([CH3:13])[CH3:12])[C:5]([NH:14][C:21](=[O:25])[CH2:22][CH2:23][CH3:24])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 8855Butyryl chlorideHCID 579081596-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine

생성물 1

HCID 57908189N-[6-chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-yl]-butyramide수율 104%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine (11.5 g, 55.2 mmol) and pyridine (13.1 g, 166 mmol) in CH2Cl2 (150 mL) was added butyryl chloride (6.5 g, 61 mmol) dropwise at 0° C. The mixture was allowed to warm to room temperature and was stirred at this temperature overnight. Water (50 mL) was added dropwise at −0° C. The resulting mixture was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude N-[6-chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-yl]-butyramide (16 g), which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ 8.72 (d, J=9.0 Hz, 1H), 7.88 (brs, 1H), 7.23 (d, J=8.4 Hz, 1H), 2.40 (d, J=7.2 Hz, 2H), 1.83-1.75 (m, 2H), 1.40 (s, 9H), 1.04 (d, J=7.2 Hz, 3H).

후처리

  1. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-8afc104524a74817b7247a8f297633bc
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563573B2

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