Diisopropylamine → 2-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(5-hydroxypent-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 30605

反応式

HRID 30605 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.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(NC(C)C)(C)C.[CH2:46]([OH:51])[CH2:47][CH2:48][C:49]#[CH:50]>C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.O.O1CCOCC1>[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:50]#[C:49][CH2:48][CH2:47][CH2:46][OH:51])[CH:20]=2)[N:3]=1

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 793464-Pentyn-1-olHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 597903072-amino-4-(3-bromophenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one

生成物 1

HCID 597903232-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(5-hydroxypent-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one収率 73.3%

試薬・触媒・溶媒 3

HCID 498840Bis(benzonitrile)palladium chloride触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (1.15 g, 2.8 mmol), dioxane, bis(benzonitrile)dichloropalladium(II) (32.2 mg, 0.084 mmol), tri-tert-butyl phosphine (10% w/w in hexane, 339 mg, 0.17 mmol) and diisopropyl amine (340 mg, 3.36 mmol) was degassed under argon for 5 minutes, treated with pent-4-yn-1-ol (236 mg, 2.8 mmol), stirred at 80° C. for 5 hours, poured into water and extracted with ethyl acetate. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue by ICSO (EtOAc/MeOH 10/1) gave the title compound as a white solid (849 mg), identified by NMR and mass spectral analyses. MS m/e [M+H]+ 414.2

後処理

  1. customwas degassed under argon for 5 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the resultant residue by ICSO (EtOAc/MeOH 10/1)

出典と根拠

ORDレコード
ord-5415d204dca748d18d663fed98bde097
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

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