Reacción #720994

Ecuación de reacción

sodium cyanoborohydride

3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde

trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine

acetic acid

→

6-{[trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamino]-methyl}-4H-benzo[1,4]oxazin-3-one

Disolventes

1,2-dichloroethane

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe reaction mixture is extracted with dichloromethane (3×10 mL)
2. 2
   SecadoThe combined organic layers are dried over sodium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   Otroto give a residue that
6. 6
   Otrois purified by preparative HPLC

Procedimiento

3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde (27 mg, 0.14 mmol, 1.0 eq) is added at room temperature to a stirred solution of trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine (47 mg, 0.14 mmol, 1.0 eq) in 1,2-dichloroethane (4 mL) and methanol (1 mL), followed by acetic acid (11 μL, 0.19 mmol, 1.3 eq) and sodium cyanoborohydride (11 mg, 0.16 mmol, 1.15 eq). After 5 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×10 mL) and a saturated sodium hydrogen carbonate aqueous solution (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by preparative HPLC to afford 6-{[trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamino]-methyl}-4H-benzo[1,4]oxazin-3-one as a white lyophilized powder (13 mg, 18% yield).

Fuente