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 448158Notes

Reaction equation

HRID 448158 reaction equation
[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

Participants

9

Reactant 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)

Product 1

HCID 673414612-[5-Bromo-4-(4-cyclopropyl-naphthalen-1-yl)-4h-[1,2,4]triazol-3-ylsulfanyl]-n-(2-chloro-4-propionylsulfamoyl-phenyl) lysinamide

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-635c88fdb0614bdab36851ec130cf499
Source dataset
uspto-grants-2013_07
Patent number
US08481581B2

Reaction notes

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