Reaktion #164584

Reaktionsgleichung

6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-4-oxo-2-phenylquinazolin-3(4H)-yl-N-isopropylacetamide

formaldehyde

cyanoborohydride

→

N-isopropyl-2-(6-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-4-oxo-2-phenylquinazolin-3(4H)-yl)acetamide

Ausbeute 39.1%

Lösungsmittel

methanol

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting solution was sealed in a microwave vial
2. 2
   SonstigeReaction mixture
3. 3
   SonstigeThe crude material was purified by SCX
4. 4
   SonstigeThe solvent was removed under reduced pressure
5. 5
   workup.DISSOLUTIONre-dissolved in methanol (1 mL)
6. 6
   Sonstigepurified by preparative-HPLC
7. 7
   SonstigePurified sample

Vorschrift

2-(6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-4-oxo-2-phenylquinazolin-3(4H)-yl-N-isopropylacetamide (EXAMPLE 4A) (100 mg, 0.23 mmol) was dissolved in acetonitrile (2 mL) before addition of formaldehyde (28 mg, 0.35 mmol) and MP-cyanoborohydride (140 mg, 0.36 mmol) followed by 2 drops of acetic acid. The resulting solution was sealed in a microwave vial and heated at 130° C. for 20 minutes. Reaction mixture was then diluted with methanol before loading directly onto a 1 g SCX cartridge. The crude material was purified by SCX. The solvent was removed under reduced pressure and then re-dissolved in methanol (1 mL) and purified by preparative-HPLC. Purified sample was free-based using 500 mg SCX cartridge to afford N-isopropyl-2-(6-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-4-oxo-2-phenylquinazolin-3(4H)-yl)acetamide (38 mg, 0.09 mmol).

Quelle