Glycine tert-butyl ester → Tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate

HRID 1631011노트

반응식

HRID 1631011 반응식
[C:1]([O:5][C:6](=[O:9])[CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[Cl:10][C:11]1[C:12](Cl)=[N:13][CH:14]=[C:15]([CH:18]=1)[C:16]#[N:17]>>[Cl:10][C:11]1[C:12]([NH:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])=[N:13][CH:14]=[C:15]([C:16]#[N:17])[CH:18]=1

참가 물질

3

반응물 2

HCID 151417Glycine tert-butyl esterHCID 128784645,6-Dichloropyridine-3-carbonitrile

생성물 1

HCID 58554110Tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate

실험 절차

A mixture of glycine tert-butyl ester (5.3 g, 40.4 mmol), TEA (5.6 mL, 40.4 mmol) and 5,6-dichloronicotinonitrile (Bionet GC-0755, 7.0 g, 40.4 mmol) was prepared and stirred at RT for 24 hours. The reaction mixture was filtered to remove inorganic solids and filtrate was concentrated under reduced pressure. The residue taken up with EtOAc (100 mL) and washed with water (2×100 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. After purification by flash chromatography (silica, pet ether/EtOAc), the title compound was obtained as a white powder. 1H NMR (DMSO-d6, 400 MHz) δ 8.41 (1H, d), 8.15 (1H, d), 7.84 (1H, t), 4.00 (2H, m), 1.38 (9H, s).

후처리

  1. customwas prepared
  2. filtrationThe reaction mixture was filtered
  3. customto remove inorganic solids and filtrate
  4. concentrationwas concentrated under reduced pressure
  5. washwashed with water (2×100 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customAfter purification by flash chromatography (silica, pet ether/EtOAc)

출처 및 근거

ORD 기록
ord-aedf92f5aac3451a867f51e4ad4d0dfb
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791142B2

반응 노트

불러오는 중…