Water → HCID 10093635, compound

HRID 1736230Notes

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:27])[CH2:25]Cl)[C:3]=1[F:28].Cl.[CH3:30][NH:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].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:27])[CH2:25][N:31]([CH3:32])[CH3:30])[C:3]=1[F:28]

Participants

Conditions

Temperature: 50 °C

Procedure

1.50 g (3.63 mmol) of Compound 159 obtained in EXAMPLE 159 was dissolved in 30 mL of dimethylformamide, 1.48 g (18.2 mmol) of dimethylamine hydrochloride and 2.50 g (18.2 mmol) of potassium carbonate 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 recrystallized from ethyl acetate/n-hexane, to give 1.18 g of Compound 161 (yield: 77%). This compound was dissolved in ethyl acetate, 3 mL of a 1N hydrochloric acid/2-propanol solution was added, and the precipitated crystals were collected by filtration, to give a hydrochloride of Compound 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 recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-169470d914574346a18899fbad40d767
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539112

Reaction notes

Loading…