Water → 2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 30577

反応式

HRID 30577 の反応式
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21](Br)[CH:20]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:11][CH:10]=2)[N:3]=1.[CH3:26][O:27][CH2:28][C:29]#[CH:30].O>N1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:11][CH:10]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:30]#[C:29][CH2:28][O:27][CH3:26])[CH:20]=2)[N:3]=1

参加物

6

反応物 3

HCID 962WaterHCID 693933-MethoxypropyneHCID 597903072-amino-4-(3-bromophenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one

生成物 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収率 63%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 31268Pyrrolidine溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (0.65 g, 1.6 mmol) in pyrrolidine was treated with 3-methoxy-propyne (0.27 mL, 3.2 mmol) followed by tetrakis(triphenylphosphine) palladium(0) (90 mg, 0.08 mmole), heated to 80° C. for 4 hrs, poured into water and extracted with ethyl acetate. The extracts were combined, washed sequentially with water and brine, dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography on silica gel in ethyl acetate to give the title product as a brown wax, 0.4 g (63% yield), identified by NMR and mass spectral analyses.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed sequentially with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by flash chromatography on silica gel in ethyl acetate

出典と根拠

ORDレコード
ord-c3329fbe5df146018136ee8d5ed1fb17
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

関連ノート

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