Triethylamine → [4-(9H-Pyrimido[4,5-b]indol-4-yl)-morpholin-2-ylmethyl]-carbamic acid tert-butyl ester
Reaktionsgleichung
Cl[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:5]=[CH:4][N:3]=1.[C:15]([O:19][C:20](=[O:29])[NH:21][CH2:22][CH:23]1[O:28][CH2:27][CH2:26][NH:25][CH2:24]1)([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CN(C=O)C>[C:15]([O:19][C:20](=[O:29])[NH:21][CH2:22][CH:23]1[O:28][CH2:27][CH2:26][N:25]([C:2]2[C:14]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6]=3[N:5]=[CH:4][N:3]=2)[CH2:24]1)([CH3:18])([CH3:16])[CH3:17]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
A mixture of 4-chloro-9H-pyrimido[4,5-b]indole (0.045 g, 0.221 mmol), morpholin-2-ylmethyl-carbamic acid tert-butyl ester (0.055 g, 0.25 mmol) and triethylamine (0.10 mL, 0.75 mmol) in DMF (0.70 mL) was heated to 120° C. in a microwave reactor for 1 hour. The cooled solution was partitioned between water (20 mL) and ethyl acetate (20 mL). The organic extract was dried (Na2SO4), filtered and concentrated. Flash column chromatography, eluting with ethyl acetate, gave the title compound as a yellow solid (0.021 g, 0.0548 mmol, 25%). LC-MS (3) Rt 5.57 min; m/z (ESI) 384 [MH+].
Aufarbeitung
- customThe cooled solution was partitioned between water (20 mL) and ethyl acetate (20 mL)
- extractionThe organic extract
- dry with materialwas dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- washFlash column chromatography, eluting with ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-7a6c4cdc0c9b4c07ac500df5ec34e625
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08618121B2
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