反应详情

A solution of 2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-9-carbaldehyde (175 mg, 0.48 mmol) and piperazine ethanol in DCE (15 mL) was treated with sodium triacetoxyborohydride (153 mg, 0.72 mmol) and catalytic acetic acid and then stirred at RT for 72 h. The resultant mixture was diluted with DCM and washed with saturated aqueous sodium hydrogen carbonate then dried (Na2SO4), filtered and concentrated in vacuo to give a colourless gum which was subjected to flash chromatography (SiO2, gradient 0-10% MeOH in DCM). The appropriate fractions were combined, concentrated in vacuo and the resultant residue dissolved in diethyl ether and treated with 1M HCl in diethyl ether (2 mL, 2 mmol). The resultant precipitate was filtered off, washed with ether and dried in vacuo to give 128 as a white solid. 1H NMR (DMSO-d6 plus deuterated TFA, 400 MHz): δ 8.22 (s, 1 H); 8.16-8.12 (m, 1 H); 7.66-7.60 (m, 1 H); 7.39 (d, J=8.3 Hz, 1 H); 7.02 (s, 1 H); 5.75 (q, J=8.7 Hz, 2 H); 4.57 (t, J=5.9 Hz, 2 H); 4.52 (s, 2 H); 3.76 (t, J=5.0 Hz, 2 H); 3.61 (br s, 8 H); 3.32 (s, 2 H); 3.24 (t, J=5.9 Hz, 2 H). 1 Exchangeable not observed. LCMS: RT=6.56 min, M+H+=478

1. washwashed with saturated aqueous sodium hydrogen carbonate
2. dry with materialthen dried (Na2SO4)
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customto give a colourless gum which
6. concentrationconcentrated in vacuo
7. dissolutionthe resultant residue dissolved in diethyl ether
8. filtrationThe resultant precipitate was filtered off
9. washwashed with ether
10. customdried in vacuo