Reaktion #1489272

Reaktionsgleichung

NH4Cl

Intermediate A

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

sodium hydride

Intermediate 5b

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

→

title compound

Ausbeute 36.8%

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

Ausbeute 36.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   SonstigeThe mixture was partitioned between water (10 mL) and ethyl acetate (3×10 mL)
3. 3
   EinengenThe aqueous phase was concentrated in vacuo
4. 4
   Sonstigethe residue purified by SCX-2
5. 5
   Wascheneluting with MeOH

Vorschrift

Intermediate A (128 mg, 0.77 mmol) was added portionwise to a suspension of sodium hydride (60% in mineral oil, 92 mg, 2.30 mmol) in dry DMF (3 mL) at RT and stirred for 15 mins. Intermediate 5b (169 mg, 0.77 mmol) was then added in one portion and the mixture heated at 60° C. for 4 h. After cooling, saturated NH4Cl (ca. 0.2 mL) was added. The mixture was partitioned between water (10 mL) and ethyl acetate (3×10 mL). The aqueous phase was concentrated in vacuo and the residue purified by SCX-2, eluting with MeOH followed by 2M NH3 in MeOH, to give the title compound as brown coloured foam (103 mg, 36%). LCMS (Method 1): Rt 1.34 min, m/z 364 [MH+].

Quelle