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Triethylamine → 2-ethoxy-N-[4-({[3-(4-fluorophenyl)isoxazol-5-yl]methyl}amino)[1,5]naphthyridin-3-yl]acetamide

HRID 606076
ノート
印刷プレビュー

反応式

HRID 606076 の反応式
[CH2:1]([O:3][CH2:4][C:5](Cl)=[O:6])[CH3:2].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][NH:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][N:30]=4)[N:25]=[CH:24][C:23]=3[NH2:32])[O:17][N:16]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][CH2:4][C:5]([NH:32][C:23]1[CH:24]=[N:25][C:26]2[C:31]([C:22]=1[NH:21][CH2:20][C:18]1[O:17][N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=3)[CH:19]=1)=[N:30][CH:29]=[CH:28][CH:27]=2)=[O:6])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chloride2 回HCID 86616886N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}[1,5]naphthyridine-3,4-diamine

生成物 1

HCID 670413032-ethoxy-N-[4-({[3-(4-fluorophenyl)isoxazol-5-yl]methyl}amino)[1,5]naphthyridin-3-yl]acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Under a nitrogen atmosphere, ethoxyacetyl chloride (1.6 g, 13 mmol) was added over a period of ten minutes to a cooled (6° C.) solution of N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}[1,5]naphthyridine-3,4-diamine (4.1 g, 12 mmol) and anhydrous triethylamine (2.6 mL, 18 mmol) in anhydrous dichloromethane (150 mL). After the reaction was stirred for 30 minutes, an analysis by HPLC indicated the presence of starting material, and additional ethoxyacetyl chloride (1.1 g) was added. The reaction was stirred for an additional 30 minutes and then was diluted with dichloromethane and washed with saturated aqueous potassium carbonate. The aqueous layer was separated and extracted with dichloromethane, and the combined organic fractions were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 2-ethoxy-N-[4-({[3-(4-fluorophenyl)isoxazol-5-yl]methyl}amino)[1,5]naphthyridin-3-yl]acetamide as a black oil.

後処理

  1. additionwas added
  2. stirringThe reaction was stirred for an additional 30 minutes
  3. washwashed with saturated aqueous potassium carbonate
  4. customThe aqueous layer was separated
  5. extractionextracted with dichloromethane
  6. washthe combined organic fractions were washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0db5512baaa44570b2d82cab71e1fc0d
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07915281B2

反応ノート

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