Trifluoroacetic acid → 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetamide

HRID 1051007ノート

反応式

HRID 1051007 の反応式
[NH2:1][C:2](=[O:36])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([S:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])=[CH:17][C:16]([CH2:26][N:27](C)[C:28](=O)OC(C)(C)C)=[CH:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]1[N:14]([S:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[O:4][CH2:3][C:2]([NH2:1])=[O:36])(=[O:12])=[O:13])[CH:15]=[C:16]([CH2:26][NH:27][CH3:28])[CH:17]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 90168683tert-butyl ((1-((3-(2-amino-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

生成物 1

HCID 747629962-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-Butyl ((1-((3-(2-amino-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 2a (100 mg, 0.19 mmol) was dissolved in 20 mL of dichloromethane. The reaction solution was cooled in an ice bath, 5 mL of trifluoroacetic acid were dropwise added, and then the reaction solution was stirred for 2 h. 50 mL of saturated sodium bicarbonate solution were added, and the reaction solution was extracted with dichloromethane (50 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system A to obtain the title product 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetamide 2 (60 mg, a yellow oil) in 75% yield.

後処理

  1. temperatureThe reaction solution was cooled in an ice bath
  2. extractionthe reaction solution was extracted with dichloromethane (50 mL×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography with elution system

出典と根拠

ORDレコード
ord-6208d864d3234a7a9ea9826fc7aaa1fb
出典データセット
uspto-grants-2016_07
特許番号
US09388133B2

反応ノート

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