Cesium carbonate → 5-(2,6-Dimethoxyphenyl)-1-(4-((4-methylthiazol-2-yl)oxy)benzyl)pyrrolidin-2-one

HRID 594677노트

반응식

HRID 594677 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:14](=[O:24])[CH2:13][CH2:12]1.Br[C:26]1[S:27][CH:28]=[C:29]([CH3:31])[N:30]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1C(=O)CCC1.Cl[Cu].C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][C:26]3[S:27][CH:28]=[C:29]([CH3:31])[N:30]=3)=[CH:21][CH:22]=2)[C:14](=[O:24])[CH2:13][CH2:12]1

참가 물질

10

반응물 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 5515412-Bromo-4-methyl-1,3-thiazoleHCID 690819375-(2,6-Dimethoxyphenyl)-1-(4-hydroxybenzyl)pyrrolidin-2-one

생성물 1

HCID 690826245-(2,6-Dimethoxyphenyl)-1-(4-((4-methylthiazol-2-yl)oxy)benzyl)pyrrolidin-2-one

시약·촉매·용매 5

HCID 62652Cuprous chloride촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

In a microwave tube, a mixture of 5-(2,6-dimethoxyphenyl)-1-(4-hydroxybenzyl)pyrrolidin-2-one (prepared as described in example 282; 60 mg; 0.18 mmol), commercially available 2-bromo-4-methylthiazole (65 mg; 0.36 mmol), Cs2CO3 (66 mg; 0.20 mmol), CuCl (9 mg; 0.09 mmol), and commercially available 2,2,6,6-tetramethylheptane-3,5-dione (34 mg; 0.18 mmol) in anh. NMP (1 ml) was sealed and irradiated by microwave (175° C.; 10 min.). Water (1 ml), AcOEt (2 ml), and toluene (1 ml) were added, and the resulting suspension was filtered over a pad of celite. The separated organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.83 min.; [M+H]+: 424.98 g/mol.

후처리

  1. customwas sealed
  2. customirradiated by microwave (175° C.; 10 min.)
  3. filtrationthe resulting suspension was filtered over a pad of celite
  4. dry with materialThe separated organic layer was dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customSubsequent purification by preparative HPLC
  8. customafforded the target compound

출처 및 근거

ORD 기록
ord-8ef7e825d1c84cb3be3d23f167fca88e
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

반응 노트

불러오는 중…