Diisopropylethylamine → 2-((3-Chloro-2-(trifluoromethyl)phenethyl)amino)-4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)pyrimidine-5-carbonitrile
Reaktionsgleichung
[OH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11](S(C)(=O)=O)[N:10]=2)[CH2:4][C:3]1([CH3:22])[CH3:21].[Cl:23][C:24]1[C:25]([C:33]([F:36])([F:35])[F:34])=[C:26]([CH2:30][CH2:31][NH2:32])[CH:27]=[CH:28][CH:29]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:23][C:24]1[C:25]([C:33]([F:34])([F:35])[F:36])=[C:26]([CH:27]=[CH:28][CH:29]=1)[CH2:30][CH2:31][NH:32][C:11]1[N:10]=[C:9]([NH:8][C@@H:5]2[CH2:6][CH2:7][C@H:2]([OH:1])[C:3]([CH3:22])([CH3:21])[CH2:4]2)[C:14]([C:15]#[N:16])=[CH:13][N:12]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A mixture of 4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile (75 mg, 0.23 mmol), 2-(3-chloro-2-(trifluoromethyl)phenyl)ethanamine (100 mg, crude) and DIEA (85 mg, 0.66 mmol) in THF (2 mL) was stirred at 100° C. in a microwave reactor for 1.5 h. After cooling to room temperature, the reaction mixture was concentrated and the residue was purified by standard methods to afford the title compound (42.2 mg, 0.090 mmol, 39% yield). 1H NMR (400 MHz, CD3OD) δ (ppm) 8.10-8.03 (m, 1H), 7.48-4.41 (m, 2H), 7.30 (m, 1H), 4.31-4.28 (m, 1H), 3.73-3.69 (m, 1H), 3.63-3.56 (m, 1H), 3.39-3.37 (m, 1H), 3.17-3.14 (m, 2H), 1.88-1.44 (m, 6H), 0.97 (s, 3H), 0.96 (s, 3H). MS (ESI) m/z 468.1 [M+H]+.
Aufarbeitung
- temperatureAfter cooling to room temperature
- concentrationthe reaction mixture was concentrated
- customthe residue was purified by standard methods
Quellen und Nachweise
- ORD-Eintrag
- ord-0827cf8c52cf444fa43a5f6ccf7c4ba7
- Quelldatensatz
- uspto-grants-2015_10
- Patentnummer
- US09156798B2
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