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Ethylmorpholine → 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole

HRID 1582657
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1582657
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH3:22])=[C:12](C(O)=O)[C:11]=2[CH:26]([CH3:28])[CH3:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.COC1C=C(OC)C=C(OC)C=1CN.C(N1CCOCC1)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH3:22])=[CH:12][C:11]=2[CH:26]([CH3:28])[CH3:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1
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Komponenten

7

Edukt 5

HCID 7525EthylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 101378285-(3,5-Dichlorophenylthio)-2-methyl-4-isopropyl-1-[(4-pyridyl)methyl]-1H-pyrrole-3-carboxylic acidHCID 162119142,4,6-Trimethoxybenzylamine hydrochloride

Produkt 1

HCID 22718399
5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole
Ausbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 160 mg of 5-(3,5-Dichlorophenylthio)-2-methyl-4-isopropyl-1-[(4-pyridyl)methyl]-1H-pyrrole-3-carboxylic acid in 10 ml of dichloromethane were added 60 mg of EDAC, 40 mg of HOBt, 68 mg of 2,4,6-trimethoxybenzylamine hydrochloride and 0.11 ml of N-ethyl morpholine. The reaction mixture was stirred at room temperature for 18 h. The reaction was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using petrol/ethyl acetate (1:4 then 1:2) then ethyl acetate for the elution to give 29 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole as an oil, mass spectrum (ESI) m/z 391 [M+H]+ and 114 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole-3-N-[(2,4,6-trimethoxy)benzyl]-carboxamide as an oil, mass spectrum (ESI) m/z 614 [M+H]+.

Aufarbeitung

  1. customThe reaction was quenched with saturated sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. wash1:2) then ethyl acetate for the elution

Quellen und Nachweise

ORD-Eintrag
ord-b84c9dec45e348fbb5542d5f995327c4
Quelldatensatz
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06737429B2

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