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

HRID 623643ノート

反応式

HRID 623643 の反応式
[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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67508828Methyl 4-((1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)carbamoyl)-6-methylpicolinate

生成物 1

HCID 675090384-((1-(5-Chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)carbamoyl)-6-methylpicolinic acid収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ec26c3aba1db480098dec36b4af6fd08
出典データセット
uspto-grants-2016_04
特許番号
US09302991B2

反応ノート

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