Hydrochloric Acid → 4-((1-(5-Chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)carbamoyl)-6-methylpicolinic acid

HRID 623643Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[CH:24]=[C:23]([CH3:25])[N:22]=[C:21]([C:26]([O:28]C)=[O:27])[CH:20]=2)=[O:18])[CH3:15])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[CH:24]=[C:23]([CH3:25])[N:22]=[C:21]([C:26]([OH:28])=[O:27])[CH:20]=2)=[O:18])[CH3:15])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:11])[F:12]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of methyl 4-((1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)carbamoyl)-6-methylpicolinate (160 mg, 0.37 mmol, Step-1, single enantiomer) in THF (5 mL) is added 2M aqueous sodium hydroxide (0.74 mL) at room temperature. The mixture is stirred at 50° C. overnight. After cooled to room temperature, the mixture is neutralized with 2M hydrochloric acid (0.74 mL) and extracted with ethyl acetate (5 mL×5). Combined organic layers are dried over sodium sulfate and concentrated under reduced pressure to give 86 mg (56% yield) of the title compound as a yellow amorphous solid.

Workup

temperatureAfter cooled to room temperature
extractionextracted with ethyl acetate (5 mL×5)
dry with materialCombined organic layers are dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ec26c3aba1db480098dec36b4af6fd08
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302991B2

Reaction notes

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