Potassium tert-butoxide → 4-(5-{2-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propyl}-4-cyclopropyl-4H-[1,2,4]triazol-3-yl)-pyridine

HRID 732137ノート

反応式

HRID 732137 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][OH:8])=[NH:6].CC(C)([O-])C.[K+].C(O[C:21](=O)[CH:22]([CH3:38])[CH2:23][C:24]1[N:28]([CH:29]2[CH2:31][CH2:30]2)[C:27]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[N:26][N:25]=1)C>C(O)CC>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:21]([CH:22]([CH3:38])[CH2:23][C:24]3[N:28]([CH:29]4[CH2:31][CH2:30]4)[C:27]([C:32]4[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=4)=[N:26][N:25]=3)[O:8][N:7]=2)[CH:9]=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 23665647Potassium tert-butoxideHCID 578380023-(4-Cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-propionic acid ethyl esterHCID 178513296HCID 178513296、化合物

生成物 1

HCID 670706264-(5-{2-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propyl}-4-cyclopropyl-4H-[1,2,4]triazol-3-yl)-pyridine収率 59%

試薬・触媒・溶媒 1

HCID 10311-Propanol溶媒

反応条件

温度
100 °C

実験手順

After 3-chloro-N-hydroxy-benzamidine (0.7 g, 4.1 mmol) was mixed with potassium-tert-butoxide (0.373 g, 3.33 mmol) in n-propanol at 80° C. for 10 min, 3-(4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-propionic acid ethyl ester (1.0 g, 3.33 mmol) was added to the reaction mixture and heated at 100° C. for 3 h. The reaction mixture was concentrated, quenched with sat. ammonium chloride and extracted with DCM. The organic layer was dried with MgSO4, purified by column chromatography and triturated with Et2O to give racemic 4-(5-{2-[3-(3-chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-propyl}-4-cyclopropyl-4H-[1,2,4]triazol-3-yl)-pyridine (0.8g, 59%). The title product (10 mg) was obtained by separation on Chiracel OJ with EtOH:hex. (1:4). 1H-NMR: 8.78(d, 2H), 8.05 (s, 1H), 7.96 (d, 1H), 7.74 (d, 2H), 7.50 (d, 1H), 7.43 (t, 1H), 4.15 (m, 1H), 3.64 (dd, 1H), 3.31 (m, 2H), 1.67 (d, 3H), 1.25 (m, 2H) and 0.78 (m, 2H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customquenched with sat. ammonium chloride
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried with MgSO4
  5. custompurified by column chromatography
  6. customtriturated with Et2O

出典と根拠

ORDレコード
ord-3c249d10a2974d2c96a037e64d098d75
出典データセット
uspto-grants-2009_09
特許番号
US07585881B2

反応ノート

読み込み中…