Hydrochloric Acid → HCID 72310560, compound

HRID 1095982Notes

Reaction equation

C[O:2][C:3](=[O:38])[C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:7]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:36])[C:22]([OH:35])([C:27]3[CH:32]=[CH:31][C:30](=[O:33])[N:29]([CH3:34])[CH:28]=3)[C:23]([F:26])([F:25])[F:24])=[C:17]([Cl:37])[CH:16]=2)=[N:6][CH:5]=1.[OH-].[Na+].Cl.CCOC(C)=O>O1CCCC1>[Cl:37][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[CH:21]([CH3:36])[C:22]([OH:35])([C:27]1[CH:32]=[CH:31][C:30](=[O:33])[N:29]([CH3:34])[CH:28]=1)[C:23]([F:26])([F:24])[F:25])[O:14][C:7]1[CH:8]=[C:9]([C:10]([F:11])([F:12])[F:13])[C:4]([C:3]([OH:38])=[O:2])=[CH:5][N:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-4-trifluoromethyl-nicotinic acid methyl ester (Example 163, 65 mg) in tetrahydrofuran (0.5 ml) was added a 1 M aqueous sodium hydroxide solution (0.23 ml) at 0° C. The mixture was stirred at 0° C. for 30 min and at room temperature for 3 h. The mixture was cooled in an ice bath. 2 M aqueous HCl (0.12 ml) and EtOAc were added. The organic phase was dried (MgSO4), filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:1=>EtOAc=>EtOAc/MeOH 4:1) to give the title compound (61 mg) as a colorless solid. MS (m/e)=551.3 [M+H+].

Workup

temperatureThe mixture was cooled in an ice bath
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:1=>EtOAc=>EtOAc/MeOH 4:1)

Sources & evidence

ORD record: ord-ecf8656e539e44a3b97a48741a993df0
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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