Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline hydrochloride

HRID 1057343

반응식

HRID 1057343 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]3[N:17]([CH3:21])[CH:18]=[CH:19][N:20]=3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.[F:22][C:23]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:24]=1[NH2:25].Cl.C(O)(C)C>CC(O)CCC.CN(C=O)C>[ClH:1].[F:22][C:23]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:24]=1[NH:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]3[N:17]([CH3:21])[CH:18]=[CH:19][N:20]=3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 219910194-Chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline

생성물 1

HCID 219910244-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline hydrochloride수율 79.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 223862-Pentanol용매

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온도
0 °C

실험 절차

A suspension of 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline (109 mg, 0.35 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (70 mg, 0.5mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (3 ml), DMF (0.5 ml) and a 5M solution of hydrogen chloride in isopropanol (74 μl, 0.35 mmol) was heated at reflux for 3 hours. The solution was then cooled to 0° C. and the resulting solid filtered off and washed with ether to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline hydrochloride as a yellow solid (124 mg, 73%).

후처리

  1. custom(prepared
  2. temperatureat reflux for 3 hours
  3. filtrationthe resulting solid filtered off
  4. washwashed with ether

출처 및 근거

ORD 기록
ord-8559c38fd7894d0ea3bd700611d90357
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514971B1

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