Diisopropylethylamine → 4-((1R,4S)-4-Hydroxy-3,3-dimethylcyclohexylamino)-2-(3-(5-methyl-1H-tetrazol-1-yl)phenethylamino)pyrimidine-5-carbonitrile

HRID 1749487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749487
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2CCN)[N:5]=[N:4][N:3]=1.[OH:16][C@H:17]1[CH2:22][CH2:21][C@@H:20]([NH:23][C:24]2[C:29]([C:30]#[N:31])=[CH:28][N:27]=[C:26](S(C)(=O)=O)[N:25]=2)[CH2:19][C:18]1([CH3:37])[CH3:36].O[C@H]1CC[C@@H:42]([NH:45]C2C(C#N)=CN=C(S(C)=O)N=2)[CH2:41]C1(C)C.CCN(C(C)C)C(C)C>>[OH:16][C@H:17]1[CH2:22][CH2:21][C@@H:20]([NH:23][C:24]2[C:29]([C:30]#[N:31])=[CH:28][N:27]=[C:26]([NH:45][CH2:42][CH2:41][C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([N:6]4[C:2]([CH3:1])=[N:3][N:4]=[N:5]4)[CH:12]=3)[N:25]=2)[CH2:19][C:18]1([CH3:37])[CH3:36]

Komponenten

5

Edukt 4

HCID 81531DiisopropylethylamineHCID 825065682-(2-(5-methyl-1H-tetrazol-1-yl)phenyl)ethanamineHCID 1181621034-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrileHCID 1181621344-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfinyl)pyrimidine-5-carbonitrile

Produkt 1

HCID 1181622534-((1R,4S)-4-Hydroxy-3,3-dimethylcyclohexylamino)-2-(3-(5-methyl-1H-tetrazol-1-yl)phenethylamino)pyrimidine-5-carbonitrileAusbeute 21 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-(2-(5-methyl-1H-tetrazol-1-yl)phenyl)ethanamine (85 mg, 0.42 mmol), 4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile and 4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfinyl)pyrimidine-5-carbonitrile (90 mg, 0.27 mmol) and DIEA (105 mg, 0.81 mmol) was stirred at 100° C. under microwave irradiation for 1.5 h. After cooling to room temperature, the reaction mixture was concentrated and the residue was purified by standard methods to give the title compound (44.3 mg, 0.073 mmol, 21% yield). 1H NMR (400 MHz, CD3OD) δ (ppm) 7.92 (m, 1H), 7.50-7.40 (m, 2H), 7.34-7.25 (m, 2H), 4.25-4.15 (m, 1H), 3.68-3.49 (m, 2H), 3.25-3.22 (m, 1H), 3.00-2.87 (m, 2H), 2.46 (s, 3H), 1.79-1.22 (m, 6H), 0.88-0.83 (m, 6H). MS (ESI) m/z 448.2 [M+H]+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by standard methods

Quellen und Nachweise

ORD-Eintrag
ord-51dfac5189ad41f8b97ac05190b80155
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156798B2

Notizen zur Reaktion

Wird geladen…