Reaktion #718021

Reaktionsgleichung

NH3

Intermediate 86c

3-(1,4-Dimethyl-piperazin-2-yl)-6-fluoro-[1,2,4]triazolo[4,3-a]pyridine

Intermediate A

(1R,4S)-4-Amino-1,2,3,4-tetrahydro-naphthalen-1-ol

NaH

→

title compound

Ausbeute 66.2%

(1S,4R)-4-[3-(1,4-Dimethyl-piperazin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamine

Ausbeute 66.2%

Lösungsmittel

DMF

MeOH

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to RT
2. 2
   SonstigeThe mixture was carefully quenched
3. 3
   workup.ADDITIONby pouring into MeOH (10 mL)
4. 4
   Waschenwashed with MeOH
5. 5
   WaschenThe product was eluted with 2M NH3 in MeOH
6. 6
   Einengenconcentration in vacuo
7. 7
   Sonstigegave a residue

Vorschrift

To a solution of Intermediate 86c (100 mg, 0.40 mmol) and Intermediate A (79 mg, 0.40 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 56 mg, 1.4 mmol) portion-wise. The mixture was stirred at 60° C. for 1.5 h then allowed to cool to RT. The mixture was carefully quenched by pouring into MeOH (10 mL) then applied to an SCX-2 cartridge and washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo gave a residue. FCC, using 0-20% [2M NH3 in MeOH] in DCM, gave the title compound as a brown oil (104 mg, 66%). LCMS (Method 4): Rt 0.26, m/z 393 [MH+].

Quelle