6-Ethoxypyridin-3-amine → 1-{[(1S,3S)-3-({[6-(ethyloxy)-3-pyridinyl]amino}methyl)-3-hydroxy-1-methylcyclohexaneyl]methyl}-1H-benzimidazole-6-carbonitrile
Reaktionsgleichung
[CH3:1][C@:2]1([CH2:10][N:11]2[C:15]3[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH2:9][CH2:8][CH2:7][C@:4]2([O:6][CH2:5]2)[CH2:3]1.[CH2:22]([O:24][C:25]1[N:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)[CH3:23]>CO>[CH2:22]([O:24][C:25]1[N:30]=[CH:29][C:28]([NH:31][CH2:5][C@:4]2([OH:6])[CH2:7][CH2:8][CH2:9][C@@:2]([CH2:10][N:11]3[C:15]4[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=4[N:13]=[CH:12]3)([CH3:1])[CH2:3]2)=[CH:27][CH:26]=1)[CH3:23]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
A 5 mL microwave vial was charged with 1-{[(3S,5S)-5-methyl-1-oxaspiro[2.5]oct-5-yl]methyl}-1H-benzimidazole-6-carbonitrile (150 mg, 0.533 mmol),6-(ethyloxy)-3-pyridinamine (221 mg, 1.599 mmol) and MeOH (4 mL). The reaction mixture was stirred and heated to 120° C. for 24 h. The reaction mixture was concentrated down to afford an oil. The oil was purified by silica gel (40 g) loading and initially elluting in DCM through to 6% MeOH/DCM over 18 column volumes to afford 1-{[(1S,3S)-3-({[6-(ethyloxy)-3-pyridinyl]amino}methyl)-3-hydroxy-1-methylcyclohexaneyl]methyl}-1H-benzimidazole-6-carbonitrile as an colorless oil. MS (m/z) 420 (M+H+).
Aufarbeitung
- concentrationThe reaction mixture was concentrated down
- customto afford an oil
- customThe oil was purified by silica gel (40 g) loading
Quellen und Nachweise
- ORD-Eintrag
- ord-64e313a5748544dc88f11002eac950c6
- Quelldatensatz
- uspto-grants-2015_11
- Patentnummer
- US09187464B2
Notizen zur Reaktion
Wird geladen…