Water → 2-[[(1S)-1-(4-fluorophenyl)ethyl]amino]-5-methyl-5-[4-(pyrrolidine-1-carbonyl)phenyl]-1,3-thiazol-4-one

HRID 46145Notes

Reaction equation

HRID 46145 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[S:12][C:13]([C:18]3[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=3)([CH3:17])[C:14](=[O:16])[N:15]=2)[CH3:9])=[CH:4][CH:3]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[S:12][C:13]([CH3:17])([C:18]3[CH:26]=[CH:25][C:21]([C:22]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[O:23])=[CH:20][CH:19]=3)[C:14](=[O:16])[N:15]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 178461992HCID 178461992, compound

Product 1

HCID 1784619932-[[(1S)-1-(4-fluorophenyl)ethyl]amino]-5-methyl-5-[4-(pyrrolidine-1-carbonyl)phenyl]-1,3-thiazol-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-((S)-1-(4-fluorophenyl)ethylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)benzoyl chloride (0.100 g, 0.26 mmol) in CH2Cl2 (1 mL) in a 0° C. bath was added pyrrolidine (Aldrich, 0.063 ml, 0.77 mmol). The mixture was gradually warmed to ambient temp. and stirred for 40 min. The reaction mixture was then added to water (5 mL), and the aqueous layer was extracted with CH2Cl2 three times. The combined organic phases were dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography. MS: 426 (M+1).

Workup

  1. temperatureThe mixture was gradually warmed to ambient temp.
  2. extractionthe aqueous layer was extracted with CH2Cl2 three times
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9d9ccb9c53dc4e5a85d3bc34550d49ce
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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