Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(3-morpholinopropoxy)cinnoline

HRID 7486

Reaction equation

HRID 7486 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[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[N:5][CH:4]=1.[F:25][C:26]1[CH:32]=[C:31]([CH3:33])[C:30]([OH:34])=[CH:29][C:27]=1[NH2:28].Cl>CC(O)CCC.C(O)(C)C>[F:25][C:26]1[CH:32]=[C:31]([CH3:33])[C:30]([OH:34])=[CH:29][C:27]=1[NH:28][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[N:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 219910584-Chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride

Product 1

HCID 219910444-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(3-morpholinopropoxy)cinnoline

Reagents, catalysts & solvents 2

HCID 3776IsopropanolCatalystHCID 223862-PentanolSolvent

Procedure

A solution of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride (132 mg, 0.33 mmol), (prepared as described for the starting material in Example 12), and 2-fluoro-5-hydroxy-4-methylaniline (56 mg, 0.39 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (2.5 ml) containing 7M hydrogen chloride in isopropanol (9drops) was heated at reflux for 30 minutes. After cooling, the solid was filtered off, washed with isopropanol, ether and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(3-morpholinopropoxy)cinnoline as an hydrochloride salt (yellow solid, 143 mg, 84%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 30 minutes
  4. temperatureAfter cooling
  5. filtrationthe solid was filtered off
  6. washwashed with isopropanol, ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-81ac5a108f83462b91d6cd5c4ab875c1
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Linked notes

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