Water → HCID 67398853, compound

HRID 70620Notes

Reaction equation

HRID 70620 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[Cl:6][C:7]1[C:8]([O:30][CH3:31])=[N:9][C:10]([C:13]([C:20]2[CH:25]=[CH:24][C:23]([S:26][CH:27]3[CH2:29][CH2:28]3)=[CH:22][CH:21]=2)=[CH:14][C@H:15]2[CH2:19][CH2:18][NH:17][CH2:16]2)=[CH:11][CH:12]=1.C(N(CC)CC)C.O>O1CCCC1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:20]2[CH:21]=[CH:22][C:23]([S:26][CH:27]3[CH2:28][CH2:29]3)=[CH:24][CH:25]=2)=[CH:14][C@H:15]2[CH2:19][CH2:18][N:17]([C:1](=[O:4])[CH2:2][CH3:3])[CH2:16]2)=[N:9][C:8]=1[O:30][CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 673995383-chloro-6-{1-[4-(cyclopropylsulfanyl)phenyl]-2-[(3R)-pyrrolidin-3-yl]ethenyl}-2-methoxypyridine

Product 1

HCID 67398853HCID 67398853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Propionyl chloride (58 μL) was added to a solution of 3-chloro-6-{1-[4-(cyclopropylsulfanyl)phenyl]-2-[(3R)-pyrrolidin-3-yl]ethenyl}-2-methoxypyridine (EZ mixture) (235 mg) and triethylamine (83 μL) in tetrahydrofuran (6 mL) under ice-cooling, and the mixture was stirred at room temperature for four hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and 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 (hexane:ethyl acetate=1:5) to give 1-[(3R)-3-{2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(cyclopropylsulfanyl)phenyl]ethenyl}pyrrolidin-1-yl]propan-1-one (EZ mixture) as a crude product (363 mg).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:5)

Sources & evidence

ORD record
ord-693fde58721a4844a1da8607afd13633
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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