1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178448506, 화합물

HRID 1693631노트

반응식

HRID 1693631 반응식
[CH2:1]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[S:7][C:6]1=[NH:12])[CH2:2][CH2:3][CH3:4].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:23][CH3:24])=[C:18]([CH:22]=1)[C:19](O)=[O:20].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:1]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[S:7]/[C:6]/1=[N:12]\[C:19](=[O:20])[C:18]1[CH:22]=[C:14]([Cl:13])[CH:15]=[CH:16][C:17]=1[O:23][CH3:24])[CH2:2][CH2:3][CH3:4]

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 769705-Chloro-o-anisic acidHCID 666431113-Butyl-5,5-dimethylthiazolidin-2-imine

생성물 1

HCID 178448506HCID 178448506, 화합물수율 40.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

A mixture of the compound from Example 2A (1.2 g, 6.4 mmol), 5-chloro-2-methoxy-benzoic acid (1.4 g, 7.7 mmol), EDCI (2.45 g, 12.8 mmol), HOBt (1.7 g, 12.8 mmol) and DMAP (78 mg, 0.64 mmol) in pyridine (40 mL) was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, diluted with water, and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, eluting with ethyl acetate/hexanes 1:3) to provide 919 mg of title compound. MS (APCI) m/z 355 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (t, J=7.4 Hz, 3H) 1.31 (m, 2H) 1.45 (s, 6H) 1.60 (m, 2H) 3.53 (m, 2H) 3.63 (t, J=7.4 Hz, 2H) 3.77 (s, 3H) 7.09 (d, J=8.9 Hz, 1H) 7.45 (dd, J=8.9, 2.8 Hz, 1H) 7.64 (d, J=2.8 Hz, 1H).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, eluting with ethyl acetate/hexanes 1:3)

출처 및 근거

ORD 기록
ord-8d47e3ba0aa54125bb6dc2d58dec851f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158663B2

반응 노트

불러오는 중…