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1,2-Dichloroethane → 2-[5-Bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4h-[1,2,4]triazol-3-ylsulfanyl]-n-(2-chloro-4-propionylsulfamoyl-phenyl) lysinamide

HRID 1844277
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1844277
[Br:1][C:2]1[N:3]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([CH:33]3[CH2:35][CH2:34]3)=[CH:25][CH:24]=2)[C:4]([S:7][CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:14][C:13]=2[Cl:22])=[O:10])=[N:5][N:6]=1.C(Cl)CCl.CC(OC(NC[CH2:49][CH2:50][CH2:51][C@H:52]([NH:56]C(OC(C)(C)C)=O)C(O)=O)=O)(C)C.C1CCC([NH:70]C2CCCCC2)CC1.[CH2:77]1C[O:80][CH2:79][CH2:78]1>CN(C1C=CN=CC=1)C.Cl.O1CCOCC1.C(Cl)Cl>[Br:1][C:2]1[N:3]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([CH:33]3[CH2:35][CH2:34]3)=[CH:25][CH:24]=2)[C:4]([S:7][C@@:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18](=[O:21])(=[O:20])[NH:19][C:79](=[O:80])[CH2:78][CH3:77])=[CH:14][C:13]=2[Cl:22])=[O:10])([CH2:49][CH2:50][CH2:51][CH2:52][NH2:56])[NH2:70])=[N:5][N:6]=1
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Komponenten

9

Edukt 4

HCID 111,2-DichloroethaneHCID 8028TetrahydrofuranHCID 115199512-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-N-(2-chloro-4-sulfamoylphenyl)acetamideHCID 12017189N2,N6-bis(tert-butoxycarbonyl)-L-lysine, compound with dicyclohexylamine (1:1)

Produkt 1

HCID 67341461
2-[5-Bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4h-[1,2,4]triazol-3-ylsulfanyl]-n-(2-chloro-4-propionylsulfamoyl-phenyl) lysinamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A 25 mL round-bottomed flask was charged with 2-[5-bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide (50 mg, 0.085 mmol), EDC (35 mg, 0.18 mmol), Boc-Lys(Boc)-OH DCHA (47 mg, 0.09 mmol) in the mixture of 5 mL THF and 5 mL methylene chloride. To the mixture was added DMAP (16 mg, 0.13 mmol) in one portion. The reaction mixture was stirred at RT for 14 h. The solvents were evaporated under reduced pressure yielding thick oily residue. The residue was dissolved in 5 mL 4.0 M HCl in dioxane. The reaction was stirred at RT for 14 h. The solvent was evaporated under reduced pressure yielding thick oily residue. The residue was washed successively with 10 mL methylene chloride and 10 mL ether yielding the title compound as a light yellow solid (44 mg, 65%).

Aufarbeitung

  1. customThe solvents were evaporated under reduced pressure
  2. customyielding thick oily residue
  3. stirringThe reaction was stirred at RT for 14 h
  4. customThe solvent was evaporated under reduced pressure
  5. customyielding thick oily residue
  6. washThe residue was washed successively with 10 mL methylene chloride and 10 mL ether yielding the title compound as a light yellow solid (44 mg, 65%)

Quellen und Nachweise

ORD-Eintrag
ord-21bd77f94b354739985039b7b8e4149a
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08946273B2

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