Water → 3-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamide

HRID 1964843Notes

Reaction equation

HRID 1964843 reaction equation
[NH2:1][C:2](=O)[CH:3]([NH:10][C:11]([CH:13]1[N:17]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:16][CH2:15][S:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C=O)C>[C:24]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:25]=[CH:26][C:21]([S:18]([N:17]2[CH2:16][CH2:15][S:14][CH:13]2[C:11]([NH:10][CH:3]([C:2]#[N:1])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:12])(=[O:19])=[O:20])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 10288863N-(2-amino-2-oxo-1-phenylethyl)-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide

Product 1

HCID 101739433-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamideYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of compound 1b, e.g., N-(2-amino-2-oxo-1-phenylethyl)-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide (385 mg, 0.8 mmol) in DMF (1 mL) at RT was added cyanuric chloride (74 mg, 0.4 mmol) in one portion. After one night, the reaction was done. Water (3 mL) was added and a precipitate was formed. The aqueous phase was extracted with two portions of EtOAc (5 mL). Combined organic phases were washed with 5% aqueous sodium bicarbonate, with water, dried over MgSO4 and concentrated under reduced pressure. A light yellow solid was isolated and was purified by flash chromatography (Cyclohexane/EtOAc gradient form 8:2 to 1:1), affording product Ic, e.g., 3-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamide (257 mg, 69% yield) in 100% purity by HPLC.

Workup

  1. waitAfter one night
  2. customa precipitate was formed
  3. extractionThe aqueous phase was extracted with two portions of EtOAc (5 mL)
  4. washCombined organic phases were washed with 5% aqueous sodium bicarbonate, with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customA light yellow solid was isolated
  8. customwas purified by flash chromatography (Cyclohexane/EtOAc gradient form 8:2 to 1:1)

Sources & evidence

ORD record
ord-330b252f48f9441fb1eaaa0019bf2c26
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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