Pyridinium chloride → HCID 178432973, compound

HRID 2387745Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:10][C@@:11]2([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)[CH2:13][C@H:12]2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([O:24]C)[N:18]=2)=[O:15])=[CH:4][N:3]=1.Cl.N1C=CC=CC=1>O>[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:10][C@@:11]2([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)[CH2:13][C@H:12]2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([OH:24])[N:18]=2)=[O:15])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of the compound 325-3 (70 mg) and pyridine hydrochloride (367 mg) was stirred at 115° C. for 2.5 hours. The temperature of the reaction solution was returned to room temperature. Thereafter, water was added to the reaction solution, and the obtained mixture was extracted with ethyl acetate. The solvent was distilled off. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate (19:1 to 0:1) to ethyl acetate:methanol (9:1)). The obtained purified product was further repurified by preparative silica gel TLC (ethyl acetate:methanol=19:1), so as to obtain the title compound (30 mg).

Workup

customwas returned to room temperature
extractionthe obtained mixture was extracted with ethyl acetate
distillationThe solvent was distilled off
customThe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate (19:1 to 0:1) to ethyl acetate:methanol (9:1))
customThe obtained purified product
customwas further repurified by preparative silica gel TLC (ethyl acetate:methanol=19:1)

Sources & evidence

ORD record: ord-9068387f68b64497bee3401721a2b656
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268848B2

Reaction notes

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