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

HRID 1806014노트

반응식

HRID 1806014 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

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).

출처 및 근거

ORD 기록
ord-df6b55dc9c404412b2cb0c95b904f62b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354540B2

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