1-Hydroxybenzotriazole → 2-Cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-{[3-(2-methoxyphenyl)-2-propene-1-yl]carbamoyl}-1,4-dihydropyridine-3-carboxylate

HRID 1700349ノート

反応式

HRID 1700349 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O-])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])[CH:5]=[CH:6][CH:7]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34]=[CH:35][CH2:36][NH2:37].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14](=[O:15])[NH:37][CH2:36][CH:35]=[CH:34][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[O:27][CH3:26])=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 37187213-(2-Methoxyphenyl)-allylamineHCID 86757801Mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

生成物 1

HCID 701567922-Cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-{[3-(2-methoxyphenyl)-2-propene-1-yl]carbamoyl}-1,4-dihydropyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

150 mg (0.416 mmol) of mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 81.4 mg (0.499 mmol) of 3-(2-methoxyphenyl)-allylamine were dissolved in 10 ml of dichloromethane. 120 mg (0.624 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 63.7 mg (0.416 mmol) of 1-hydroxybenzotriazole were added to the obtained solution under cooling with ice, and they were stirred at room temperature for 2 hours. Dichloromethane was evaporated under reduced pressure. Ethyl acetate was added to the residue, and the product was washed with 1 N hydrochloric acid and then with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1) to obtain the title compound.

後処理

  1. temperatureunder cooling with ice, and they
  2. customDichloromethane was evaporated under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. washthe product was washed with 1 N hydrochloric acid
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1)

出典と根拠

ORDレコード
ord-a0f5701b66e2472a81e4804a782331ab
出典データセット
uspto-grants-2002_02
特許番号
US06350762B1

反応ノート

読み込み中…