Water → HCID 58452509, compound

HRID 70643Notes

Reaction equation

O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[C:16]([C:20]1[CH:25]=[CH:24][C:23](/[C:26](/[C:45]2[CH:50]=[CH:49][C:48]([O:51][CH:52]([F:54])[F:53])=[C:47]([O:55]CC3C=CC(OC)=CC=3)[N:46]=2)=[CH:27]\[C@@H:28]2[N:32](CC3C=CC(OC)=CC=3OC)[C:31](=[O:44])[CH2:30][CH2:29]2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>C(Cl)(Cl)Cl>[C:16]([C:20]1[CH:21]=[CH:22][C:23](/[C:26](/[C:45]2[NH:46][C:47](=[O:55])[C:48]([O:51][CH:52]([F:53])[F:54])=[CH:49][CH:50]=2)=[CH:27]\[C@H:28]2[CH2:29][CH2:30][C:31](=[O:44])[NH:32]2)=[CH:24][CH:25]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 65 °C

Procedure

Water (0.4 mL) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.72 g) were added to a solution of (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-{5-(difluoromethoxy)-6-[(4-methoxybenzyl)oxy]-pyridin-2-yl}ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (511 mg) in chloroform (8 mL), and the mixture was stirred at 65° C. for 16 hours. Water was added to the reaction solution. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1→chloroform:methanol=1:0→95:5→9:1) to give the title compound as a colorless oil (96 mg).

Workup

filtrationAfter filtration
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1→chloroform:methanol=1:0→95:5→9:1)

Sources & evidence

ORD record: ord-3e50b27580ac4901b4dfa94127c97c6b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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