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 732137노트

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HRID 732137 반응식
[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

참가 물질

5

반응물 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, 화합물

생성물 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)-pyridine수율 59%

시약·촉매·용매 1

HCID 10311-Propanol용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3c249d10a2974d2c96a037e64d098d75
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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