Isopropanol → 4-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride

HRID 7503

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride (150 mg, 0.36 mmol), (prepared as described for the starting material in Example 12), 4-chloro-2-fluoroaniline (77 mg, 0.53 mmol) in 2-pentanol (4 ml) and 5M isopropanolic hydrogen chloride (1 ml) was heated at 120° C. for 1 hour. The mixture was allowed to cool and isopropanol was added. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride (185 mg, 98%).

Workup

temperatureto cool
filtrationThe resulting precipitate was collected by filtration
washwashed with ether
customdried under vacuum

Sources & evidence

ORD record: ord-0b7086452ac64a56a87f5db7ea740a99
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087602B2

Linked notes

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