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Lithium Hydroxide → 2-{3-(4-Chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N-{2-formamido-2-[3-(trifluoromethyl)phenyl]ethyl}acetamide

HRID 709157
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 709157
C(N(CC)C(C)C)(C)C.Cl.[NH2:11][CH:12]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=1)[CH2:13][NH:14][C:15](=[O:37])[CH2:16][N:17]1[C:21](=[O:22])[N:20]([CH2:23][C@H:24]([OH:29])[C:25]([F:28])([F:27])[F:26])[C:19]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[N:18]1.[CH:48](OC1C=CC([N+]([O-])=O)=CC=1)=[O:49].[OH-].[Li+]>C1COCC1.O>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([C:19]2[N:20]([CH2:23][C@H:24]([OH:29])[C:25]([F:28])([F:27])[F:26])[C:21](=[O:22])[N:17]([CH2:16][C:15]([NH:14][CH2:13][CH:12]([NH:11][CH:48]=[O:49])[C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=3)=[O:37])[N:18]=2)=[CH:35][CH:34]=1
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Komponenten

7

Edukt 4

HCID 3939Lithium HydroxideHCID 746284-Nitrophenyl formateHCID 81531DiisopropylethylamineHCID 89765105N-{2-Amino-2-[3-(trifluoromethyl)phenyl]ethyl}-2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetamide hydrochloride

Produkt 1

HCID 56848556
2-{3-(4-Chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N-{2-formamido-2-[3-(trifluoromethyl)phenyl]ethyl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

20 μl (112 μmol) of N,N-diisopropylethylamine were added to a solution of 60 mg (102 μmol) of the compound of Example 58A in 1 ml of THF. The mixture was cooled to 0° C., 18 mg (107 μmol) of 4-nitrophenyl formate were then added a little at a time and stirring was continued at 0° C. for 1 h. Since LC/MS analysis of the reaction mixture indicated the additional formation of an O-formylated byproduct, 408 μl of a 1 N solution of lithium hydroxide in water were added to the reaction mixture. Stirring of the mixture was then continued at RT overnight. The volatile components were then removed on a rotary evaporator. The residue was dissolved in a little DMSO and separated by preparative HPLC [Method 8]. The product-containing fraction was freed from the solvent on a rotary evaporator and the residue was dried under high vacuum. This gave 35 mg (59% of theory) of the title compound.

Aufarbeitung

  1. additionwere added to the reaction mixture
  2. stirringStirring of the mixture
  3. waitwas then continued at RT overnight
  4. customThe volatile components were then removed on a rotary evaporator
  5. dissolutionThe residue was dissolved in a little DMSO
  6. customseparated by preparative HPLC [Method 8]
  7. customThe product-containing fraction was freed from the solvent on a rotary evaporator
  8. customthe residue was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e5a06f9af4d24d07a31e1c4cf7985c87
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09180120B2

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