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-(3-methoxypropyl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 30579노트

반응식

HRID 30579 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>[Pd]>[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]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH:10]=2)[N:3]=1

참가 물질

3

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 161142522-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxypropyl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one수율 40%

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

A mixture of an ethanolic 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) and 10% palladium on charcoal (10 mg) was placed under a hydrogen filled balloon for 16 h and filtered thru celite. The filtrate was concentrated to dryness in vacuo. The resultant residue was purified by flash chromatography on silica gel, ethyl acetate as eluent, to give the title product as a white solid, 0.04 g (40% yield), mp 48-50° C.; 1H NMR (DMSO-d6) δ 2.4 (m, 2H); 2.95 (s, 3H); 3.2 (s, 3H); 3.3 (t, 2H); 6.6 (b, 2H); 7.1 (m, 3H); 7.2 (m, 4H); 7.4 (d, 2H); MS [(+)ESI] m/z=404 [M−H]+.

후처리

  1. customfor 16 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness in vacuo
  4. customThe resultant residue was purified by flash chromatography on silica gel, ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-f63714413e8d4eeea544ecc2eb22c284
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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