2-Pentanol → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-methoxy-7-(3-pyrrolidinopropoxy)cinnoline

HRID 1057340

반응식

HRID 1057340 반응식
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:10](OC)[CH:11]=2)[N:6]=[N:5][CH:4]=1.[F:24][C:25]1[CH:31]=[C:30]([CH3:32])[C:29]([OH:33])=[CH:28][C:26]=1[NH2:27].C[CH:35]([OH:39])CCC>>[F:24][C:25]1[CH:31]=[C:30]([CH3:32])[C:29]([OH:33])=[CH:28][C:26]=1[NH:27][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)=[CH:10][CH:11]=2)[N:6]=[N:5][C:4]=1[O:39][CH3:35]

참가 물질

4

반응물 3

HCID 223862-PentanolHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 219910394-Chloro-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline hydrochloride

생성물 1

HCID 696632464-(2-Fluoro-5-hydroxy-4-methylanilino)-methoxy-7-(3-pyrrolidinopropoxy)cinnoline

실험 절차

A solution of 4-chloro-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline hydrochloride (158 mg, 0.4 mmol),(prepared as described for the starting material in Example 13), and 2-fluoro-5-hydroxy-4-methylaniline (67 mg, 0.48 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (5 ml) was heated at reflux for 1 hour. After cooling, the solid was filtered off, washed with isopropanol, ether and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-methoxy-7 (3-pyrrolidinopropoxy)cinnoline as the hydrochloride salt (yellow solid, 55 mg, 27%).

후처리

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 1 hour
  4. temperatureAfter cooling
  5. filtrationthe solid was filtered off
  6. washwashed with isopropanol, ether
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-74e682908b094c95b5c3c9041345db2f
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514971B1

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