1,2-Dichloroethane → N-[2-(Carbamoylamino)-1-(2,3-dichlorophenyl)ethyl]-2-[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetamide

HRID 2402844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2402844
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:11](=[O:19])[N:10]([CH2:20][C:21](O)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.[CH2:24]([Cl:27])[CH2:25][Cl:26].[CH:28]1[CH:29]=[CH:30][C:31]2[N:36](O)N=[N:34][C:32]=2[CH:33]=1.C(N(CC)C(C)C)(C)C.C[N:48]([CH:50]=[O:51])C>C(OCC)(=O)C>[C:50]([NH:34][CH2:32][CH:31]([NH:36][C:21](=[O:22])[CH2:20][N:10]1[C:11](=[O:19])[N:12]([CH2:13][CH2:14][C:15]([F:18])([F:16])[F:17])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1)[C:30]1[CH:29]=[CH:28][CH:33]=[C:25]([Cl:26])[C:24]=1[Cl:27])(=[O:51])[NH2:48]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59536724[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

Produkt 1

HCID 46917113N-[2-(Carbamoylamino)-1-(2,3-dichlorophenyl)ethyl]-2-[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Of the compound from Example 177A, 162 mg (0.46 mmol), 145 mg (0.51 mmol) of the compound from Example 153A, 107 mg (0.56 mmol) of EDC, 75 mg (0.56 mmol) of HOBt and 97 μl (0.56 mmol) of N,N-diisopropylethylamine were stirred in 5.4 ml of DMF at RT overnight. The solution was diluted with 150 ml of ethyl acetate and extracted in succession twice each with 1M hydrochloric acid and with 1M aqueous sodium hydrogen carbonate solution. The organic phase was dried over sodium sulphate and freed from the volatile components on a rotary evaporator. The residue was purified by preparative HPLC [Method 20]. The product fraction was freed from the solvents on a rotary evaporator and the residue was dried in an HV. This gave 163 mg (61% of theory) of the title compound.

Aufarbeitung

  1. extractionextracted in succession twice each with 1M hydrochloric acid
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customfreed from the volatile components on a rotary evaporator
  4. customThe residue was purified by preparative HPLC [Method 20]
  5. customThe product fraction was freed from the solvents on a rotary evaporator
  6. customthe residue was dried in an HV

Quellen und Nachweise

ORD-Eintrag
ord-378c7b76f2d64fa19802b8fb96f42fd7
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796324B2

Notizen zur Reaktion

Wird geladen…