Hydrochloric Acid → 2-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-2-methyl-propionamide

HRID 333823

反応式

HRID 333823 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([OH:23])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11].Br[C:25]([CH3:30])([CH3:29])[C:26]([NH2:28])=[O:27].[OH-].[Na+].Cl>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11])[O:23][C:25]([CH3:30])([CH3:29])[C:26]([NH2:28])=[O:27]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2 回HCID 1012352-Bromo-2-methylpropanamide2 回HCID 574212643-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol

生成物 1

HCID 574212652-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-2-methyl-propionamide

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol (Example 133, 200 mg) and 2-bromo-2-methyl-propionamide (272 mg) in dimethyl acetamide (1 mL) were treated with sodium hydroxide (66 mg) and stirred at r.t. for 17 h. A second portion of 2-bromo-2-methyl-propionamide (272 mg) followed by sodium hydroxide (66 mg) was added and the reaction mixture further stirred for 2 h at r.t. This process was repeated a last time and the reaction mixture was diluted with ice-water (10 mL), neutralized with 1N aqueous HCl, extracted with ethyl acetate (2×), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (20 g silica gel, ethyl acetate/heptane 1:2) to give the title compound as off-white waxy solid (170 mg). MS (m/e)=451.0 (MH+).

後処理

  1. additionwas added
  2. stirringthe reaction mixture further stirred for 2 h at r.t
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (20 g silica gel, ethyl acetate/heptane 1:2)

出典と根拠

ORDレコード
ord-a96b5cd409304b4699b22d5d76106504
出典データセット
uspto-grants-2014_11
特許番号
US08883786B2

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