Acetyl chloride → N-[6-[2-(4-Cyano-phenyl)-4-methyl-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide
Reaktionsgleichung
[CH3:1][C:2]1[C:7]([C:8](=O)[CH2:9][CH3:10])=[CH:6][N:5]2[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[N:14]=[C:4]2[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1.[NH:29]([C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=1)[NH2:30].[C:39](Cl)(=O)C.BrC1C(C)=C(C2C=CC=C(C(F)(F)F)C=2)C2N(N=C(NC(=O)C)N=2)C=1>>[C:35]([C:34]1[CH:37]=[CH:38][C:31]([N:29]2[C:8]([C:7]3[C:2]([CH3:1])=[C:3]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=4)[C:4]4[N:5]([N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[N:14]=4)[CH:6]=3)=[C:9]([CH3:10])[CH:39]=[N:30]2)=[CH:32][CH:33]=1)#[N:36]Komponenten
5
Edukt 4
Produkt 1
Versuchsvorschrift
The title compound was prepared from N-[7-methyl-6-propionyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide (Int. 26, 11 mg, 0.023 mmol) and 4-hydrazino-benzonitrile (7 μL, 0.051 mmol) using similar methods to those employed in Example 40, Steps 3 and 4. During step 4 the acetyl group was lost, which was re-introduced by reaction with acetyl chloride using a similar method to that used for Intermediate 18 to give the title compound as a cream solid (3 mg).
Quellen und Nachweise
- ORD-Eintrag
- ord-046e41a9a0d840c8a0ac68c9b47295a1
- Quelldatensatz
- uspto-grants-2015_12
- Patentnummer
- US09199984B2
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