2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one → 2-Amino-5-[4-(difluoromethoxy)phenyl]-5-{3-[(1Z)-3-methoxyprop-1-en-1-yl]phenyl}-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 30578

반응식

HRID 30578 반응식
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]([F:29])[F:28])=[CH:22][CH:21]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][CH2:17][O:18][CH3:19])[CH:10]=2)[N:3]=1>C(O)C.N1C2C(=CC=CC=2)C=CC=1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH:27]([F:29])[F:28])=[CH:24][CH:25]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11](/[CH:15]=[CH:16]\[CH2:17][O:18][CH3:19])[CH:10]=2)[N:3]=1

참가 물질

5

반응물 1

HCID 574358862-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

생성물 1

HCID 161141572-Amino-5-[4-(difluoromethoxy)phenyl]-5-{3-[(1Z)-3-methoxyprop-1-en-1-yl]phenyl}-3-methyl-3,5-dihydro-4H-imidazol-4-one수율 50%

시약·촉매·용매 3

HCID 7047Quinoline촉매HCID 131709914Lindlars catalyst촉매HCID 702Ethanol용매

실험 절차

A mixture of a solution of 2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (0.1 g, 0.25 mmol) in ethanol (1.5 mL), quinoline (1 drop) and Lindlar catalyst (24 mg. 10% mol) was placed under a hydrogen filled balloon, stirred for 16 hr filtered through celite. The filtrate was concentrated in vacuo. The resultant residue was purified by flash chromatography on silica ge,l ethyl acetate as eluent, to afford the title compound as a white solid, 0.05 g (50% yield), mp 41-44° C.; 1H NMR (DMSO-d6) δ 2.95 (s, 3H); 3.2 (s, 3H); 4.0 (d, 2H); 5.7 (q, 1H) 6.5 (d, 1H); 6.6 (b, 2H); 7.1 (m, 3H); 7.3 (m, 4H); 7.4 (d, 2H); MS [(+)ESI] m/z=402 [M−H]+.

후처리

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe resultant residue was purified by flash chromatography on silica ge,l ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-d381bb94e1de42e783452cf2a60f271e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

연결된 노트

불러오는 중…