5-Amino-4-fluoro-2-methylphenol → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride

HRID 7492

Reaction equation

HRID 7492 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[N:5][CH:4]=1.[F:23][C:24]1[CH:30]=[C:29]([CH3:31])[C:28]([OH:32])=[CH:27][C:25]=1[NH2:26]>CC(O)CCC>[ClH:2].[F:23][C:24]1[CH:30]=[C:29]([CH3:31])[C:28]([OH:32])=[CH:27][C:25]=1[NH:26][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[N:5][CH:4]=1

Participants

4

Reactant 2

HCID 101540985-Amino-4-fluoro-2-methylphenolHCID 219910114-Chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride

Product 1

HCID 219910554-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochlorideYield 29.3%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

A solution of 4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride (268 mg, 0.71 mmol), (prepared as described for the starting material in Example 10), and 2-fluoro-5-hydroxy-4-methylaniline, (109 mg, 0.77 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (6 ml) was heated at reflux for 4 hours. After dilution with isopropanol the solid was filtered off, washed with isopropanol followed by ether to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride (92 mg, 29%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 4 hours
  4. filtrationAfter dilution with isopropanol the solid was filtered off
  5. washwashed with isopropanol

Sources & evidence

ORD record
ord-ede3ca8d119b49a8ac2e73f1d9c835b8
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Linked notes

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