Aluminium lithium hydride → HCID 24826338、化合物

反応式

[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:18]=[C:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[C:11]([C:12](OCC)=[O:13])=[CH:10][N:9]=2)[S:5][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]([CH2:12][OH:13])=[C:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[CH:18]=2)[S:5][CH:6]=1

参加物

実験手順

A solution of ethyl 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinate (1.50 g, 3.70 mmol) in THF (15 mL) was added to a 1.0 M solution of lithium aluminum hydride (18.5 mL, 18.5 mmol) in ether at 0° C. and stirred for 30 minutes. The reaction was quenched with sodium sulfate decahydrate, stirred 30 minutes, and filtered. The solids were washed with THF, filtered, and concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried, and concentrated. The residue was triturated with hexanes and filtered to afford (6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)pyridin-3-yl)methanol (1.10 g, 81.8% yield) as a white solid. 1H NMR (DMSO-d6) δ 10.68 (bs, 1H), 8.25 (s, 1H), 8.05 (d, 1H), 7.92 (d, 2H), 7.53-7.64 (m, 3H), 7.36 (d, 1H), 6.47 (s, 1H), 6.19 (s, 1H), 5.20 (t, 1H), 4.71 (d, 2H), 2.13 (s, 3H); Mass spectrum (esi) m/z=364 (100) (M+H).