Dimethylformamide → 3-(5-chloro-3-pyridyloxy)-N-(1-chloro-3-methylbut-1-yn-3-yl)butyramide

HRID 1374892노트

반응식

HRID 1374892 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:13][CH3:14])[C:10](O)=O)[CH:5]=[N:6][CH:7]=1.CN(C)C=[O:18].C(Cl)(=O)C(Cl)=O.Cl.[Cl:27][C:28]#[C:29][C:30]([NH2:33])([CH3:32])[CH3:31]>ClCCl.CN(C)C1C=CN=CC=1.CCCCCC.C(OCC)(=O)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH3:10])[CH2:13][C:14]([NH:33][C:30]([CH3:32])([CH3:31])[C:29]#[C:28][Cl:27])=[O:18])[CH:5]=[N:6][CH:7]=1

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 210783581-Chloro-3-amino-3-methylbut-1-yne hydrochlorideHCID 210783782-(5-Chloro-3-pyridyloxy)butyric acid

생성물 1

HCID 210784103-(5-chloro-3-pyridyloxy)-N-(1-chloro-3-methylbut-1-yn-3-yl)butyramide

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매3회HCID 8471Triethylamine용매HCID 21226206Ethyl acetate hexane용매

실험 절차

2-(5-Chloro-3-pyridyloxy)butyric acid (0.35 g; prepared as described in Stage 2 of Example 1) was stirred in dry dichloromethane (5 ml) containing N,N-dimethylformamide (0.1 ml) and treated dropwise with oxalyl chloride (0.145 ml) at ambient temperature. The solution was stirred for 0.5 hours and added in portions to a mixture of 1-chloro-3-amino-3-methylbut-1-yne hydrochloride (0.25 g; prepared as described below), dry triethylamine (0.68 ml) and 4-dimethylaminopyridine (0.01 g) in dry dichloromethane (5 ml) with stirring at ambient temperature. The mixture was stirred for 1 hour, stored for 18 hours, diluted with further dichloromethane, washed with aqueous sodium hydrogen carbonate, dried over magnesium sulphate and evaporated under reduced pressure to give an oil. The oil was fractionated by chromatography (silica:hexane/ethyl acetate 3:1 by volume) to give a solid that was recrystallised from hexane to give the required product as a colourless solid, 0.15 g, m.p. 78–82° C.

후처리

  1. stirringwith stirring at ambient temperature
  2. stirringThe mixture was stirred for 1 hour
  3. waitstored for 18 hours
  4. washwashed with aqueous sodium hydrogen carbonate
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customto give a solid
  9. customthat was recrystallised from hexane

출처 및 근거

ORD 기록
ord-46b9e99c369242969a0eb112830f4f40
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166621B2

반응 노트

불러오는 중…