5-Amino-2-chloro-4-fluorophenol → 7-Benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxycinnoline

HRID 7470

Reaction equation

HRID 7470 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14](Cl)=[CH:15][N:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:23][C:24]1[C:30]([OH:31])=[CH:29][C:27]([NH2:28])=[C:26]([F:32])[CH:25]=1>CN(C=O)C>[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:28][C:27]3[CH:29]=[C:30]([OH:31])[C:24]([Cl:23])=[CH:25][C:26]=3[F:32])=[CH:15][N:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 219910077-Benzyloxy-4-chloro-6-methoxycinnoline hydrochloride

Product 1

HCID 219910477-Benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxycinnoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride (3.4 g, 10 mmol) and 4-chloro-2-fluoro-5-hydroxyaniline, (prepared as described in EP 061741 A2), (1.84 g, 11 mmol) in DMF (42 ml) was heated at 130° C. for 20 minutes. The resulting solid was filtered off, washed with isopropanol, ether and dried under vacuum to give 7-benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxycinnoline as the hydrochloride salt (yellow solid. 3.5 g, 75%).

Workup

  1. filtrationThe resulting solid was filtered off
  2. washwashed with isopropanol, ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-62d71bbbedcf4e048364ce7e5a1dabe2
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Linked notes

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