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 1404538ノート

反応式

HRID 1404538 の反応式
[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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67979270N-((R)-1-{5-[5-Chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-acetamide

生成物 1

HCID 68484636(R)-1-{5-[5-Chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethylamine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-024976ebaae44f90a5329c0c2f1a17e8
出典データセット
uspto-grants-2014_12
特許番号
US08912221B2

反応ノート

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