Reaktion #717968

Reaktionsgleichung

Intermediate 62b

6-Fluoro-3-((S)-1-methyl-piperidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine

NaH

Intermediate A

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

→

title compound

Ausbeute 71.1%

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

Ausbeute 71.1%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled
2. 2
   Sonstigequenched by dropwise addition of methanol
3. 3
   workup.ADDITIONbefore being diluted with methanol
4. 4
   Waschenwas washed with MeOH and product
5. 5
   Wascheneluted with 2M NH3 in MeOH
6. 6
   SonstigeThe resulting residue was purified by FCC

Vorschrift

To a suspension of NaH (60% in mineral oil, 171 mg, 4.27 mmol) in DMF (4.00 mL) was added Intermediate A (175 mg, 1.07 mmol) and the reaction stirred for 20 min. Intermediate 62b (250 mg, 1.07 mmol) was added in DMF (2.00 mL) and the reaction heated to 60° C. for one hour. The reaction was cooled and quenched by dropwise addition of methanol, before being diluted with methanol and loaded onto an SCX-2 cartridge, which was washed with MeOH and product eluted with 2M NH3 in MeOH. The resulting residue was purified by FCC, using 2-10% [2M NH3 in MeOH] in DCM, to give the title compound (287 mg, 71%). LCMS (Method 1): Rt 1.64, m/z 378.2 [MH+].

Quelle