1,2-Dichloro-3-isocyanatobenzene → 1-(5-tert-butyl-2-(5-oxo-1,4-diazepane-1-carbonyl)-1H-pyrrol-3-yl)-3-(2,3-dichloro-phenyl)urea

HRID 18928ノート

反応式

HRID 18928 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:17]([CH3:20])([CH3:19])[CH3:18])[NH:5][C:6]=1[C:7]([N:9]1[CH2:15][CH2:14][C:13](=[O:16])[NH:12][CH2:11][CH2:10]1)=[O:8].[Cl:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[N:29]=[C:30]=[O:31]>C1COCC1.C(OCC)(=O)C>[C:17]([C:4]1[NH:5][C:6]([C:7]([N:9]2[CH2:15][CH2:14][C:13](=[O:16])[NH:12][CH2:11][CH2:10]2)=[O:8])=[C:2]([NH:1][C:30]([NH:29][C:23]2[CH:24]=[CH:25][CH:26]=[C:27]([Cl:28])[C:22]=2[Cl:21])=[O:31])[CH:3]=1)([CH3:20])([CH3:19])[CH3:18]

参加物

5

反応物 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 586792281-(4-amino-2-tert-butyl-1H-pyrrole-5-carbonyl)-1,4-diazepan-5-one

生成物 1

HCID 586791281-(5-tert-butyl-2-(5-oxo-1,4-diazepane-1-carbonyl)-1H-pyrrol-3-yl)-3-(2,3-dichloro-phenyl)urea収率 50%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

The previously prepared 1-(4-amino-2-tert-butyl-1H-pyrrole-5-carbonyl)-1,4-diazepan-5-one (8 mg, 0.03 mmol) and 2,3 dichlorophenyl isocyanate (5 mg, 0.03 mmol) were dissolved in THF (2 mL) and heated at 70° C. for 2 hours. The reaction mixture was cooled down to room temperature, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, dried and the solvent eliminated under vacuum. The crude product was purified by preparative thin layer chromatography using a mixture of dichloromethane:methanol 9:1 as elution solvent to afford 7.0 mg of 1-(5-tert-butyl-2-(5-oxo-1,4-diazepane-1-carbonyl)-1H-pyrrol-3-yl)-3-(2,3-dichloro-phenyl)urea as a white solid. 1H NMR (400 MHz, acetone-d6): δ (ppm) 9.60 (bs, 1H); 8.60 (d, 2H); 8.26 (d, 1H); 7.30 (t, 1H); 7.20 (d, 1H); 6.84 (t, 1H); 6.59 (d, 1H); 3.76 (m, 2H); 3.70 (m, 2H); 3.40 (m, 2H); 2.61 (m, 2H); 1.37 (s, 9H).

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. washwashed with saturated aqueous sodium bicarbonate
  3. customdried
  4. customThe crude product was purified by preparative thin layer chromatography
  5. additiona mixture of dichloromethane:methanol 9:1
  6. washas elution solvent

出典と根拠

ORDレコード
ord-b6ec3c39b59d45f9a0e6cc05adbd1477
出典データセット
uspto-grants-2010_06
特許番号
US07741479B2

反応ノート

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