Water → HCID 9890493, compound

HRID 1736232Notes

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].[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.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:27])[CH2:25][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C:3]=1[F:28]

Participants

Conditions

Temperature: 50 °C

Procedure

515 mg (1.25 mmol) of Compound 159 obtained in EXAMPLE 159 was dissolved in 10 mL of dimethylformamide, 0.62 mL (6.2 mmol) of piperidine and 0.22 mL (1.25 mmol) of diisopropylethylamine were added, and the mixture was stirred at 50° C. for 2 hours. 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:acetonitrile=4:1) and recrystallized from ethyl acetate, to give 441 mg of Compound 164 (yield: 77%).

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:acetonitrile=4:1)
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-4a61825413b647f9973a1ebb3c454185
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539112

Reaction notes

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