Formic Acid → 4-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylpiperazine-1-carbaldehyde

HRID 2105989ノート

反応式

HRID 2105989 の反応式
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]([OH:28])([CH2:15][C:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])([CH3:18])[CH3:17])[C:11]([F:14])([F:13])[F:12])[CH2:3]1.[CH:29](OC=O)=[O:30].C(N=C=NC(C)C)(C)C.C(O)=O>C(Cl)Cl.N1C=CC=CC=1>[F:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][CH3:27])=[C:19]([C:16]([CH3:18])([CH3:17])[CH2:15][C:10]([OH:28])([C:11]([F:12])([F:13])[F:14])[CH2:9][N:4]2[CH2:3][CH:2]([CH3:1])[N:7]([CH:29]=[O:30])[CH:6]([CH3:8])[CH2:5]2)[CH:24]=1

参加物

7

反応物 4

HCID 284Formic AcidHCID 12734DiisopropylcarbodiimideHCID 9548680Formic anhydride2 回HCID 57809802HCID 57809802、化合物

生成物 1

HCID 103428654-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylpiperazine-1-carbaldehyde

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(3,5-dimethylpiperazin-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (20 mg) in methylene chloride (1 mL) at 0° C. was added pyridine (60.7 μL) followed by formic anhydride (2M in methylene chloride, 0.5 mL). (Formic anhydride was freshly prepared by slow addition of one equivalent of 1,3-diisopropylcarbodiimide to 2 equivalents of formic acid in methylene chloride. The resulting suspension was stirred for 1 hour, and filtered). The resulting mixture was stirred overnight for 20 hours, filtered through a cotton plug, poured into half-saturated aqueous sodium bicarbonate solution, and extracted twice with methylene chloride. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluted with 5% methanol-methylene chloride) to give the title compound as a clear oil (19.3 mg).

後処理

  1. filtrationfiltered)
  2. stirringThe resulting mixture was stirred overnight for 20 hours
  3. filtrationfiltered through a cotton plug
  4. additionpoured into half-saturated aqueous sodium bicarbonate solution
  5. extractionextracted twice with methylene chloride
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (eluted with 5% methanol-methylene chloride)

出典と根拠

ORDレコード
ord-370790d94eb9424484f8c5e28901e465
出典データセット
uspto-grants-2009_08
特許番号
US07579469B2

反応ノート

読み込み中…