Hydrochloric Acid → N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-3-yl)pyridin-2-amine dihydrochloride

HRID 1806014ノート

反応式

HRID 1806014 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:13]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:12][C:11]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:10][N:9]=2)[S:5][CH:6]=1.[ClH:27]>C(Cl)Cl.CCOCC>[ClH:27].[ClH:27].[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:13]([O:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:12][C:11]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:10][N:9]=2)[S:5][CH:6]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 24765544N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-3-yl)pyridin-2-amine

生成物 1

HCID 86631469N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-3-yl)pyridin-2-amine dihydrochloride収率 59.71%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

5-Bromo-N-(4-methylthiazol-2-yl)-3-phenoxypyridin-2-amine (0.070 g, 0.1932 mmol), pyridin-3-ylboronic acid (0.02850 g, 0.2319 mmol), Pd(PPh3)4 (0.02233 g, 0.01932 mmol), DME (10 mL), and 2M sodium bicarbonate (2 mL) were combined, heated to 80° C. and stirred overnight. The reaction mixture was cooled and partitioned between CH2Cl2 and water. The organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography (30-40% EtOAc in hexane) to give N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-3-yl)pyridin-2-amine. N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-3-yl)pyridin-2-amine was dissolved in CH2Cl2 and 2M HCl in ether was added to give N-(4-methylthiazol-2-yl)-3-phenoxy-5-(pyridin-3-yl)pyridin-2-amine dihydrochloride (0.050 g, 59.71% yield). 1H NMR (d6-DMSO) δ 9.19 (d, 1H), 8.78 (dd, 1H), 8.70 (m, 2H), 7.93 (m, 2H), 7.42 (t, 2H), 7.18 (t, 1H), 7.12 (d, 2H), 6.74 (s, 1H), 2.28 (s, 3H); Mass spectrum (apci) m/z=361.2 (M+H-2HCl).

出典と根拠

ORDレコード
ord-df6b55dc9c404412b2cb0c95b904f62b
出典データセット
uspto-grants-2013_01
特許番号
US08354540B2

反応ノート

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