Water → 4-[2-(2,4-dichlorophenyl)-5-methyl-4-({[5-(trifluoromethyl)pyridin-2-yl]amino}carbonyl)-1H-imidazol-1-yl]phenyl 3-methylbutane-1-sulfonate

HRID 1715108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1715108
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[C:11]([CH3:27])=[C:12]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)=[O:15])[N:13]=1.C(N(CC)CC)C.[CH3:42][CH:43]([CH3:50])[CH2:44][CH2:45][S:46](Cl)(=[O:48])=[O:47].O>ClCCl>[CH3:42][CH:43]([CH3:50])[CH2:44][CH2:45][S:46]([O:34][C:31]1[CH:30]=[CH:29][C:28]([N:10]2[C:11]([CH3:27])=[C:12]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][N:18]=3)=[O:15])[N:13]=[C:9]2[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[CH:33][CH:32]=1)(=[O:48])=[O:47]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 129333273-Methylbutane-1-sulfonyl chlorideHCID 685074162-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)-5-methyl-N-[5-(trifluoromethyl)pyridin-2-yl]-1H-imidazole-4-carboxamide

Produkt 1

HCID 115998914-[2-(2,4-dichlorophenyl)-5-methyl-4-({[5-(trifluoromethyl)pyridin-2-yl]amino}carbonyl)-1H-imidazol-1-yl]phenyl 3-methylbutane-1-sulfonateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)-5-methyl-N-[5-(trifluoromethyl)pyridin-2-yl]-1H-imidazole-4-carboxamide, prepared as described in Ex. 13, Step 3 (139 mg, 0.27 mmol) and triethylamine (46 μl, 0.33 mmol) in dichloromethane (4.0 ml) were cooled to −78° C. 3-Methylbutane-1-sulfonyl chloride (56 mg, 0.33 mmol) was carefully added to the reaction mixture. The resulting mixture was stirred at −78° C. for 1 h, and then allowed to reach room temperature. Water was added to the reaction, and the phases were separated. The organic phase was washed with NaHCO3, brine and dried with Na2SO4. The solvent was removed under reduced pressure and separation by preparatory HPLC gave the title compound (81 mg, 46%) as a solid.

Aufarbeitung

  1. customto reach room temperature
  2. customthe phases were separated
  3. washThe organic phase was washed with NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed under reduced pressure and separation by preparatory HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c625d70380e6435b8eba3dd1efc86452
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799804B2

Notizen zur Reaktion

Wird geladen…