Water → HCID 11797134, compound

HRID 1736231Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

130 mg (0.276 mmol) of Compound 160 obtained in EXAMPLE 160 was dissolved in 5 mL of dimethylformamide, 112 mg (1.38 mmol) of dimethylamine hydrochloride and 0.24 mL (1.38 mmol) of diisopropylethylamine were added, and the mixture was stirred at 50° C. for 30 minutes. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=9:1), to give 122 mg of Compound 162 (yield: 86%), which was converted to a hydrochloride according to the same manner as that in EXAMPLE 161.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialan aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record: ord-76ec97d07a964a3991fda263204ddeb5
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539112

Reaction notes

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