1,2-二氯乙烷 → 2,2-Dimethyl-N-[1-[6-(5-{2-[4-(trifluoromethyl)phenyl]ethyl}-1,2,4-oxadiazol-3-yl)quinolin-2-yl]pyrrolidin-3-yl}propanamide

HRID 6815

反应方程式

HRID 6815 反应方程式
[OH:1][NH:2][C:3](=[NH:26])[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([N:14]1[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15]1)[CH:8]=[CH:7]2.[F:27][C:28]([F:41])([F:40])[C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:39])C(O)=O)=[CH:31][CH:30]=1.[CH2:42](Cl)CCl>COCCOCCOC>[CH3:24][C:21]([CH3:22])([CH3:23])[C:20]([NH:19][CH:16]1[CH2:17][CH2:18][N:14]([C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[CH:12][CH:13]=[C:4]([C:3]4[N:26]=[C:42]([CH2:39][CH2:35][C:32]5[CH:31]=[CH:30][C:29]([C:28]([F:27])([F:40])[F:41])=[CH:34][CH:33]=5)[O:1][N:2]=4)[CH:5]=3)[N:10]=2)[CH2:15]1)=[O:25]

参与物

5

反应物 3

HCID 111,2-二氯乙烷HCID 102424842-[4-(三氟甲基)苯基]丙酸HCID 178419012HCID 178419012，化合物

产物 1

HCID 220189022,2-Dimethyl-N-[1-[6-(5-{2-[4-(trifluoromethyl)phenyl]ethyl}-1,2,4-oxadiazol-3-yl)quinolin-2-yl]pyrrolidin-3-yl}propanamide

试剂、催化剂与溶剂 1

HCID 8150二乙二醇二甲醚溶剂

反应条件

温度
50 °C

实验过程

To a mixture of the product of Step E, (66 mg) in anhydrous diglyme (2 mL) was added 4-trifluoromethylphenylpropionic acid (1.1 eq.) and EDC (2 eq.). The reaction mixture was heated to 50° C. overnight. After approximately 18 h, the mixture was heated at 110° C. for 2 hr. The mixture was cooled to r.t., quenched with water and extracted with excess EtOAc. The combined extracts were dried over a drying agent filtered and the solvent removed under vacuum. The residue was purified by preparative TLC eluting with EtOAc to afford the product, MS: m/z 538.

后处理

  1. temperaturethe mixture was heated at 110° C. for 2 hr
  2. temperatureThe mixture was cooled to r.t.
  3. customquenched with water
  4. extractionextracted with excess EtOAc
  5. customThe combined extracts were dried over a drying agent
  6. filtrationfiltered
  7. customthe solvent removed under vacuum
  8. customThe residue was purified by preparative TLC
  9. washeluting with EtOAc
  10. customto afford the product, MS

来源与证据

ORD记录
ord-5b2ee72421e84c96a53e63a90b2cd355
来源数据集
uspto-grants-2006_08
专利号
US07084156B2

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