Acetonitrile → HCID 59251035, Verbindung

HRID 218178

Reaktionsgleichung

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:24])([CH3:23])[C:18]([CH3:22])([CH3:21])[CH2:19][NH2:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[S:25]1[CH:29]=[CH:28][N:27]=[C:26]1[NH:30][C:31](=O)[O:32]C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.C(#N)C>CO.C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:24])([CH3:23])[C:18]([CH3:22])([CH3:21])[CH2:19][NH:20][C:31]([NH:30][C:26]4[S:25][CH:29]=[CH:28][N:27]=4)=[O:32])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutan-1-amine (10 mg, 0.031 mmol), phenyl thiazol-2-ylcarbamate (15 mg, 0.068 mmol), diisopropylethylamine (0.1 mL), and anhydrous acetonitrile (0.1 mL) was stirred under nitrogen at 80° C. till the reaction completed (ca 30 min) The mixture was dissolved in methanol and TFA. Purification using reverse phase HPLC (YMC S5 20×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA) gave the title compound (4 mg, 0.009 mmol, 29% yield) as a white solid. MS found: (M+H)+=452. 1H-NMR (400 MHz, CHLOROFORM-d) δ ppm 8.16 (s, 1 H) 7.79 (s, 1 H) 7.69 (dd, J=8.90, 4.83 Hz, 2 H) 7.60 (d, J=9.10 Hz, 1 H) 7.52 (dd, J=9.10, 1.70 Hz, 1 H) 7.21-7.31 (m, 3 H) 6.91 (d, J=4.07 Hz, 1 H) 5.56 (t, J=6.00 Hz, 1 H) 3.28 (d, J=6.10 Hz, 2 H) 1.52 (s, 6 H) 0.96 (s, 6 H).

Aufarbeitung

custom(ca 30 min)
customPurification
customphase HPLC (YMC S5 20×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag: ord-9399435b433a47249ae04f7a44bed427
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08198311B2

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