Methanol → HCID 11374592, compound

Participants

Reaction Steps

A solution of (7RS,9aRS)-5-(7-aminomethyl-octahydro-pyrido[1,2-a]pyrazin-2-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (1 eq.; see Example 9 above) and pyridine-4-carbaldehyde (1 eq.) in anhydrous THF was treated with titanium (IV) isopropoxide (1.7 eq.) at around 60° C. for 5 hours. To the mixture was added anhydrous methanol, and followed by the careful addition of NaBH4 (1.5 eq). After one hour, the reaction was completed as indicated by HPLC analysis. The solvent was removed and the residue was purified by preparative HPLC using aqueous CH3CN (buffered with 0.1% TFA) to afford (7RS,9aRS)-2-furan-2-yl-5-(7-{[(pyridin-4-ylmethyl)-amino]-methyl}-octahydro-pyrido[1,2-a]pyrazin-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine as a white powder: 1H NMR (400 MHz, CD3OD) δ 1.77-2.11 (m, 4H), 2.66 (m, 1H), 3.78-3.05 (m, 1H), 4.46 (bs, 2H), 6.65 (dd, J=1.8, 3.4 Hz, 1H), 7.18 (d, J=3.4 Hz, 1H), 7.74 (d, J=1.8 Hz, 1H), 7.88 (d, J=6.0 Hz, 2H), 8.81 (d, J=6.0 Hz, 2H). MS m/z: 461 [M+H]+.

Provenance & Evidence