Dimethylamine → HCID 57898973、化合物

反応式

[CH3:1][NH:2][CH3:3].[CH3:4][C:5]1[N:6]=[C:7]([NH:10][C:11]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:14]([CH:15]=O)=[CH:13][N:12]=2)[S:8][CH:9]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH3:1][N:2]([CH2:15][C:14]1[C:17]([O:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[CH:18][C:11]([NH:10][C:7]2[S:8][CH:9]=[C:5]([CH3:4])[N:6]=2)=[N:12][CH:13]=1)[CH3:3]

参加物

実験手順

Dimethylamine (0.374 mL, 0.747 mmol) was added to a solution of 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinaldehyde (0.090 g, 0.249 mmol) in THF (3 mL) and stirred for 10 minutes. Sodium triacetoxyborohydride (0.264 g, 1.25 mmol) was added and the reaction mixture was stirred for an additional 30 minutes. The mixture was quenched with saturated sodium bicarbonate, partitioned between ethyl acetate and water, washed with brine, dried, and concentrated. The residue was dissolved in THF (2 mL), 1M HCl in ether was added, the solution was diluted in hexanes (5 mL), triturated for 15 minutes, filtered, dried to afford 5-((dimethylamino)methyl)-N-(4-methylthiazol-2-yl)-4-(naphthalen-1-yloxy)pyridin-2-amine (0.071 g, 73.0% yield) as a white solid. 1H NMR (DMSO d6) δ 10.88 (bs, 1H), 8.58 (s, 1H), 8.09 (d, 1H), 7.98 (d, 1H), 7.90 (d, 1H), 7.52-7.67 (m, 4H), 6.67 (s, 1H), 6.37 (s, 1H), 4.54 (s, 2H), 2.88 (s, 6H), 2.18 (s, 3H).