Sodium Hydroxide → 2-[4-(3-dimethylaminopropylamino)-3-fluorophenyl]-6,8-difluoro-5-pentylamino-4H-1-benzopyran-4-one

HRID 1736198Notes

Reaction equation

C([N:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[C:24]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:20]=3[C:21](=[O:23])[CH:22]=2)=[CH:13][C:12]=1[F:36])[CH2:5][CH2:6][CH2:7][N:8]([CH3:10])[CH3:9])(=O)C.[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:10][N:8]([CH3:9])[CH2:7][CH2:6][CH2:5][NH:4][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[C:24]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:20]=3[C:21](=[O:23])[CH:22]=2)=[CH:13][C:12]=1[F:36]

Participants

Conditions

Temperature: 80 °C

Procedure

10 mL of concentrated sulfuric acid was added to 725 mg (1.44 mmol) of the above 2-[4-[N-acetyl-N-(3-dimethylaminopropyl)amino]-3-fluorophenyl]-6,8-difluoro-5-pentylamino-4H-1-benzopyran-4-one and the mixture was stirred at 80° C. for 20 minutes. The reaction solution was poured into ice water, the mixture was adjusted to pH 7 by addition of a 10N aqueous solution of sodium hydroxide thereto, and the precipitated crystals were collected by filtration. The crystals were purified by silica gel column chromatography (chloroform:methanol=20:1-9:1) and recrystallized from ethyl acetate/n-hexane to give 473 mg of Compound 127 (yield: 71%), which was converted to hydrochloride according to the conventional method.

Workup

filtrationthe precipitated crystals were collected by filtration
customThe crystals were purified by silica gel column chromatography (chloroform:methanol=20:1-9:1)
customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-d262ef6b37ea4e48af3a01d07d14eeb7
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539112

Reaction notes

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