5-Amino-2-chloro-4-fluorophenol → 4-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline

HRID 7483

Reaction equation

HRID 7483 reaction equation
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]([O:13][CH3:14])[CH:11]=2)[N:6]=[N:5][CH:4]=1.[Cl:24][C:25]1[C:31]([OH:32])=[CH:30][C:28]([NH2:29])=[C:27]([F:33])[CH:26]=1>CC(O)CCC>[Cl:24][C:25]1[C:31]([OH:32])=[CH:30][C:28]([NH:29][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[N:5][CH:4]=2)=[C:27]([F:33])[CH:26]=1

Participants

4

Reactant 2

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 219910394-Chloro-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline hydrochloride

Product 1

HCID 219910334-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

A solution of 4-chloro-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline hydrochloride (0.1 g, 0.25 mmol) and 4-chloro-2-fluoro-5-hydroxyaniline (57 mg, 0.35 mmol), (prepared as described in EP 061741 A2), in 2-pentanol (5 ml) was heated at 120° C. for 2.5 hours. The solid was filtered off, washed with isopropanol and then ether and dried under vacuum to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(3-pyrrolidinopropoxy)cinnoline as the hydrochloride salt (yellow solid, 94 mg, 72%).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with isopropanol
  3. dry with materialether and dried under vacuum

Sources & evidence

ORD record
ord-83bb9ee9edd94868a9d634d247df59ab
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Linked notes

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