Dimethylamine → HCID 67399343, compound

HRID 70665Notes

Reaction equation

HRID 70665 reaction equation
[CH3:1][NH:2][CH3:3].CS(O[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[C:14]([O:48][CH3:49])=[N:15][C:16](/[C:19](/[C:38]2[CH:43]=[CH:42][C:41]([C:44]([CH3:47])([CH3:46])[CH3:45])=[CH:40][CH:39]=2)=[CH:20]/[C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[O:36][CH3:37])=[CH:17][CH:18]=1)(=O)=O>>[C:44]([C:41]1[CH:40]=[CH:39][C:38](/[C:19](/[C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][N:2]([CH3:3])[CH3:1])=[C:14]([O:48][CH3:49])[N:15]=2)=[CH:20]\[C@@H:21]2[N:22]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=3[O:36][CH3:37])[C:23](=[O:26])[CH2:24][CH2:25]2)=[CH:43][CH:42]=1)([CH3:47])([CH3:46])[CH3:45]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 86658012HCID 86658012, compound

Product 1

HCID 67399343HCID 67399343, compound

Procedure

Triethylamine (50 μL) and methanesulfonyl chloride (25 μL) were added to a solution of (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(4-hydroxybutyl)-6-methoxypyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (144 mg) in chloroform (2 mL), and the mixture was stirred at room temperature for three hours. Triethylamine (50 μL) and methanesulfonyl chloride (25 μL) were further added thereto and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 4-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)butyl methanesulfonate as a crude product. 2 M dimethylamine (solution in methanol) (3 mL) was added to 4-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)butyl methanesulfonate, and the mixture was stirred at room temperature for 17 hours. The solvent was evaporated from the reaction solution and then water was added, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:0→4:1) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-{5-[4-(dimethylamino)butyl]-6-methoxypyridin-2-yl}ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless oil.

Workup

  1. customThe solvent was evaporated from the reaction solution
  2. additionwater was added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customafter which the solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:0→4:1)

Sources & evidence

ORD record
ord-43af19a6cccc46d29f54b2592c4f7428
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…