Triethylamine → N-(4-chloro-2-methylphenyl)-N'-(2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethyl)urea

HRID 1162360

反応式

HRID 1162360 の反応式
Cl.Cl.[NH2:3][CH:4]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([N:13]2[CH2:17][C:16]3=[CH:18][N:19]=[C:20]([CH3:21])[N:15]3[C:14]2=[O:22])[CH2:9][CH2:8]1)=[O:6].C(N(CC)CC)C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]=[C:44]=[O:45])=[C:39]([CH3:46])[CH:38]=1>C(#N)C>[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]([NH:3][CH:4]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:5]([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[CH2:17][C:16]4=[CH:18][N:19]=[C:20]([CH3:21])[N:15]4[C:14]3=[O:22])[CH2:9][CH2:8]2)=[O:6])=[O:45])=[C:39]([CH3:46])[CH:38]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1421574-Chloro-2-methylphenyl isocyanateHCID 23138338HCID 23138338、化合物

生成物 1

HCID 23138117N-(4-chloro-2-methylphenyl)-N'-(2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethyl)urea収率 64.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2-(1-(2-Amino-2-phenylacetyl)-4-piperidinyl)-5-methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride (0.21 g) obtained in Example 115a) was dissolved in acetonitrile (5.0 ml). Triethylamine (0.14 ml) and 4-chloro-2-methylphenyl isocyanate (80 mg) were added thereto, and mixed at room temperature for 15 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The reaction mixture was washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate). The product was crystallized from ethyl acetate-diethyl ether to obtain the title compound as colorless powder (0.16 g, 61%).

後処理

  1. additionmixed at room temperature for 15 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe reaction mixture was washed with an aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified with basic silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)
  8. customThe product was crystallized from ethyl acetate-diethyl ether

出典と根拠

ORDレコード
ord-2892fbdaf70440ae97e28f2102919493
出典データセット
uspto-grants-2010_10
特許番号
US07820673B2

関連ノート

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