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

HRID 1964843
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HRID 1964843 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-330b252f48f9441fb1eaaa0019bf2c26
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415480B2

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