Methyl-d3-amine → 5-{1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}imidazo[5,1-f][1,2,4]triazin-4-amine
Reaktionsgleichung
C[C:2]1[N:10]2[C:5]([C:6](=O)[NH:7][CH:8]=[N:9]2)=[C:4]([C:12]2[CH:13]=[N:14][N:15]([CH3:27])[C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[N:3]=1.[2H]C([NH2:32])([2H])[2H]>>[CH3:27][N:15]1[C:16]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=2)=[C:12]([C:4]2[N:3]=[CH:2][N:10]3[C:5]=2[C:6]([NH2:32])=[N:7][CH:8]=[N:9]3)[CH:13]=[N:14]1Komponenten
Versuchsvorschrift
7-Methyl-5-{1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}imidazo[5,1-f][1,2,4]triazin-4(3H)-one was converted to the product according to the general procedure for the synthesis of 4-(azetidin-1-yl)-7-methyl-5-(1-methyl-1H-pyrazol-4-yl)imidazo[1,5-f][1,2,4]triazine in Example 2, except that methyl-d3-amine was used in place of azetidine hydrochloride. In this case, the reaction was worked up via removal of solvent in vacuo, followed by addition of water and extraction with ethyl acetate. The combined organic layers were concentrated under reduced pressure and purified using silica gel chromatography (Gradient: 0% to 100% [5% methanol/5% triethylamine/90% ethyl acetate] in heptane) to afford the product as a gummy oil. Yield: 20 mg, 0.051 mmol, 42%. LCMS m/z 391.4 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.57 (s, 3H), 3.94 (s, 3H), 7.51 (br d, J=8.1 Hz, 2H), 7.70 (br d, J=8.2 Hz, 2H), 7.75 (s, 1H), 7.79 (s, 1H)
Aufarbeitung
- customIn this case, the reaction was worked up via removal of solvent in vacuo
- additionfollowed by addition of water and extraction with ethyl acetate
- concentrationThe combined organic layers were concentrated under reduced pressure
- custompurified
Quellen und Nachweise
- ORD-Eintrag
- ord-5639495c2d7641d2b2825fce43fe5f71
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08598155B2
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