Hydrochloric Acid → {3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-4-yl}-acetonitrile

HRID 1096000Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]#[N:32])=[CH:26][CH:25]=2)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:23])[C:9]([OH:22])([C:14]1[CH:15]=[N:16][C:17]([O:20]C)=[CH:18][CH:19]=1)[C:10]([F:13])([F:12])[F:11].Cl.O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]#[N:32])=[CH:26][CH:25]=2)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:23])[C:9]([OH:22])([C:14]1[CH:19]=[CH:18][C:17](=[O:20])[NH:16][CH:15]=1)[C:10]([F:12])([F:11])[F:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of {3′-chloro-4′-[3,3,3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-biphenyl-4-yl}-acetonitrile (87 mg) in dioxane (2.8 ml) was added conc. aqueous HCl (0.31 ml). The mixture was stirred at 100° C. for 1.5 h. After cooling to room temperature, water was added and the mixture was extracted with EtOAc. The organic phase was concentrated to dryness and the product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1) to give the title compound (59 mg) as a colorless solid. MS (m/e)=447.3 [M+H+].

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted with EtOAc
concentrationThe organic phase was concentrated to dryness
customthe product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1)

Sources & evidence

ORD record: ord-081b673388e14027acdcab0ced9eb59b
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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