Hydrochloric Acid → (R)-1-{5-[5-Chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethylamine

HRID 1404538Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([F:27])[C:5]([C:21]2[N:25]=[C:24]([CH3:26])[O:23][N:22]=2)=[C:6]([C:8]2[CH:9]=[C:10]([F:20])[C:11]([C@H:14]([NH:16]C(=O)C)[CH3:15])=[N:12][CH:13]=2)[CH:7]=1.Cl.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([F:27])[C:5]([C:21]2[N:25]=[C:24]([CH3:26])[O:23][N:22]=2)=[C:6]([C:8]2[CH:9]=[C:10]([F:20])[C:11]([C@H:14]([NH2:16])[CH3:15])=[N:12][CH:13]=2)[CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A suspension of N—((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-acetamide (195 mg, 0.496 mmol, step A) in 2N HCl (2.5 ml, 5.00 mmol) was heated to 75° C. overnight. The colorless solution was cooled to room temperature, diluted with water and the pH was adjusted to 12 by addition of 1N NaOH. The mixture was then extracted three times with EtOAc and the combined organic layers were washed with brine (pH adjusted to 12 with 1N NaOH), dried with Na2SO4 and evaporated. The crude title compound (167 mg, 96%, light yellow gum) was used in the next reaction step without further purification. MS: 351.1 [M+H]+.

Workup

temperatureThe colorless solution was cooled to room temperature
extractionThe mixture was then extracted three times with EtOAc
washthe combined organic layers were washed with brine (
dry with materialdried with Na2SO4
customevaporated
customThe crude title compound (167 mg, 96%, light yellow gum) was used in the next reaction step without further purification

Sources & evidence

ORD record: ord-024976ebaae44f90a5329c0c2f1a17e8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912221B2

Reaction notes

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