Diisopropylethylamine → Methyl {1-[(4-chlorophenyl)(phenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate

HRID 1724186노트

반응식

HRID 1724186 반응식
Br[CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.[NH:16]1[CH2:19][CH:18]([CH:20]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=2)[C:21]([O:23][CH3:24])=[O:22])[CH2:17]1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:24][O:23][C:21](=[O:22])[C:20](=[C:18]1[CH2:17][N:16]([CH:2]([C:3]2[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:19]1)[C:25]1[CH:26]=[C:27]([F:32])[CH:28]=[C:29]([F:31])[CH:30]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 113805081-[Bromo(phenyl)methyl]-4-chlorobenzeneHCID 67065947Methyl azetidin-3-yl(3,5-difluorophenyl)acetate

생성물 1

HCID 67065891Methyl {1-[(4-chlorophenyl)(phenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 0.280 g (1 mmol) of 1-[bromo(phenyl)methyl]-4-chlorobenzene, 0.120 g (0.5 mmol) of methyl azetidin-3-yl(3,5-difluorophenyl)acetate (Example 22, Step 1) and 0.12 mL (0.7 mmol) of diisopropylethylamine in 10 mL of acetonitrile was heated at 40° C. for 18 h. The solution was concentrated and the residue was dissolved in 20 mL of ethyl acetate. This solution was washed with 10 mL water and the aqueous layer was washed with a second aliquot of 20 mL ethyl acetate. The organic extracts were washed with brine, combined, and concentrated. The residue was dissolved in acetonitrile and purified by reverse phase chromatography (Waters Xterra C18, 19 mm×50 mm) using a gradient of acetonitrile-water-triethylamine (30:70:1 to 60:40:1) to afford the title compound; 1NMR(CDCl3) δ 3.74 (s, 3H), 3.88 (m, 2H), 4.24 (m, 2H), 4.55 (s, 1H), 6.70-6.86 (m, 3H), 7.21-7.43 (m, 9H); Mass Spectrum: m/e=440 (M+1 35Cl) and 442 (M+1 37Cl).

후처리

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in 20 mL of ethyl acetate
  3. washThis solution was washed with 10 mL water
  4. washthe aqueous layer was washed with a second aliquot of 20 mL ethyl acetate
  5. washThe organic extracts were washed with brine
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in acetonitrile
  8. custompurified by reverse phase chromatography (Waters Xterra C18, 19 mm×50 mm)

출처 및 근거

ORD 기록
ord-1ef77606aa744fc48bc9a59f6632a5d4
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485732B2

반응 노트

불러오는 중…