Tetrahydrofuran → 1-(5-Tert-butyl-2-(1-(2-(dimethylamino)ethyl)-3,3-dimethyl-2-oxopiperazine-4-carbonyl)thiophen-3-yl)-3-(2,3-dichlorophenyl)urea

HRID 18924ノート

反応式

HRID 18924 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:23]([CH3:26])([CH3:25])[CH3:24])[S:5][C:6]=1[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:11](=[O:20])[C:10]1([CH3:22])[CH3:21])=[O:8].[Cl:27][C:28]1[C:29]([Cl:37])=[C:30]([N:34]=[C:35]=[O:36])[CH:31]=[CH:32][CH:33]=1.C1COCC1>C(OCC)(=O)C>[C:23]([C:4]1[S:5][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]([CH3:18])[CH3:19])[C:11](=[O:20])[C:10]2([CH3:21])[CH3:22])=[O:8])=[C:2]([NH:1][C:35]([NH:34][C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([Cl:27])[C:29]=2[Cl:37])=[O:36])[CH:3]=1)([CH3:26])([CH3:25])[CH3:24]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 586791234-(4-Amino-2-tert-butylthiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-one

生成物 1

HCID 586794051-(5-Tert-butyl-2-(1-(2-(dimethylamino)ethyl)-3,3-dimethyl-2-oxopiperazine-4-carbonyl)thiophen-3-yl)-3-(2,3-dichlorophenyl)urea収率 66.9%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

A mixture of 4-(4-amino-2-tert-butylthiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-one (0.035 g, 0.092 mmol), dichlorophenyl isocyanate (0.019 g, 0.10 mmol), and THF (2 mL) was heated at 75° C. for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, dried, the solvent eliminated under vacuum and the crude product was purified by preparative thin layer chromatography (dichloromethane:methanol, 95:5) to afford 0.035 g of 1-(5-tert-butyl-2-(1-(2-(dimethylamino)ethyl)-3,3-dimethyl-2-oxopiperazine-4-carbonyl)thiophen-3-yl)-3-(2,3-dichlorophenyl)urea. 1H NMR (400 MHz, acetone-d6): δ (ppm) 9.57 (bs, 1H); 8.86 (bs, 1H); 8.17 (d, 1H); 7.65 (s, 1H); 7.30 (m, 2H); 3.90 (m, 2H); 3.60 (m, 2H); 3.50 (t, 2H); 2.43 (t, 2H); 2.20 (s, 6H); 1.70 (s, 6H); 1.40 (s, 9H).

後処理

  1. washwashed with saturated sodium bicarbonate
  2. customdried
  3. customthe crude product was purified by preparative thin layer chromatography (dichloromethane:methanol, 95:5)

出典と根拠

ORDレコード
ord-9d86c46e42b3410b98ab25d58e8b0204
出典データセット
uspto-grants-2010_06
特許番号
US07741479B2

反応ノート

読み込み中…