Diisopropylethylamine → HCID 57725706, Verbindung
Reaktionsgleichung
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.[NH2:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[OH:21].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]3[OH:21])[S:3][C:4]=2[CH:10]=1Komponenten
5
Reaktionsbedingungen
- Temperatur
- 115 °C
Versuchsvorschrift
To a solution of 2-chloro-6-methoxybenzo[d]thiazole (1.0 g, 5 mmol) in 5.5 mL of NMP was added (1R,2R)-2-aminocyclohexanol hydrochloride (910 mg, 6 mmol) and DIPEA (2.44 mL, 14 mmol). The reaction solution was stirred at 115° C. for 96 hours. The crude reaction solution was purified by preparative HPLC to give purified fractions that was combined and neutralized with solid NaHCO3. The resulting solution was extracted with EtOAc (2×300 mL). The combined organic layers were washed with water (60 mL) and brine (60 mL), then dried over Na2SO4 and evaporated in vacuo to give (1R,2R)-2-(6-methoxybenzo[d]thiazol-2-ylamino)cyclohexanol (1.06 g, 3.81 mmol) as an ivory solid. ES/MS m/z 279.1 (MH+).
Aufarbeitung
- customThe crude reaction solution
- customwas purified by preparative HPLC
- customto give
- custompurified fractions that
- extractionThe resulting solution was extracted with EtOAc (2×300 mL)
- washThe combined organic layers were washed with water (60 mL) and brine (60 mL)
- dry with materialdried over Na2SO4
- customevaporated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-3cf5d74336ad44d1a5e9a1171f80d1e2
- Quelldatensatz
- uspto-grants-2012_10
- Patentnummer
- US08293769B2
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