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

反応式

HRID 30578 の反応式
[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

参加物

5

反応物 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

生成物 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-one収率 50%

試薬・触媒・溶媒 3

HCID 7047Quinoline触媒HCID 131709914Lindlars catalyst触媒HCID 702Ethanol溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-d381bb94e1de42e783452cf2a60f271e
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

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