Trifluoroacetic acid → HCID 86706417, Verbindung

HRID 577423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577423
CS[C:3]1[N:4]=[N:5][C:6]([C:17]([NH2:19])=[O:18])=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:8]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.CCN(C(C)C)C(C)C.Cl.[NH2:41][C@H:42]([CH2:46][CH3:47])[C:43]([NH2:45])=[O:44].C(O)(C(F)(F)F)=O>CN1C(=O)CCC1.O>[NH2:45][C:43](=[O:44])[C@H:42]([NH:41][C:3]1[N:4]=[N:5][C:6]([C:17]([NH2:19])=[O:18])=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:8]=1)[CH2:46][CH3:47]

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 16218339(2R)-2-aminobutanamide hydrochlorideHCID 867064153-(Methylthio)-5-(p-tolylamino)-1,2,4-triazine-6-carboxamide

Produkt 1

HCID 86706417HCID 86706417, VerbindungAusbeute 132,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

3-(Methylthio)-5-(p-tolylamino)-1,2,4-triazine-6-carboxamide (31 mg, 0.11 mmol) was dissolved in 5 mL NMP. To it was added mCPBA (77%) (100 mg, 0.44 mmol). The mixture was stirred at RT for 1 h. To it was added DIEA (0.20 mL, 1.1 mmol) and (R)-2-aminobutanamide hydrochloride (77 mg, 0.55 mmol). The mixture was stirred at 80° C. for 2.5 h. The mixture was cooled to RT, acidified with TFA (0.3 mL), diluted with water, filtered and subjected to reverse phase preparative HPLC to isolate the title compound (48 mg) as HCl salt. MS found for C15H19N7O2 as (M+H)+ 330.4. UV: λ=235, 278 nm. Proton NMR: (CD3OD) δ 7.60 (2H, d, J=8.0 Hz), 7.28 (2H, d, J=8.0 Hz), 4.40 (1H, dd, J=8.0; 5.2 Hz), 2.36 (3H, s), 2.00 (1H, m), 1.90 (1H, m), 1.05 (3H, t, J=7.2 Hz) ppm.

Aufarbeitung

  1. stirringThe mixture was stirred at 80° C. for 2.5 h
  2. temperatureThe mixture was cooled to RT
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-ff784fef541448fc99a72bc99a1ecc87
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040530B2

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