Dimethylformamide → N-(4-(4-amino-2-fluorophenoxy)pyridin-2-yl)morpholine-4-carboxamide

HRID 492761ノート

反応式

HRID 492761 の反応式
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[CH:6]=1.[Cl-].[NH4+].CN(C)C=O>C(O)C.[Fe].O.C(OCC)(=O)C>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[O:13])[CH:6]=2)=[C:2]([F:1])[CH:23]=1

参加物

8

反応物 3

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57677388N-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]morpholine-4-carboxamide

生成物 1

HCID 57677752N-(4-(4-amino-2-fluorophenoxy)pyridin-2-yl)morpholine-4-carboxamide収率 87.9%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

To a suspension of morpholine-4-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide (941 mg) in ethanol (50 ml) were added water (10 ml), electrolytic iron powder (581 mg), ammonium chloride (1.11 g) and N,N-dimethylformamide (0.75 ml), followed by stirring to heat at 90° C. for 30 min. The reaction mixture was cooled down to room temperature, and filtered to remove an insoluble portion, which was washed with water and N,N-dimethylformamide in this order. The filtrate was concentrated under a reduced pressure to give a residue, to which ethyl acetate (100 ml) and water (100 ml) were added to partition. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; hexane:ethyl acetate=1:1 to 1:2, ethyl acetate, then ethyl acetate:methanol=20:1 to 10:1). Fractions containing the target compound were concentrated to provide the titled compound (759 mg, 87.8%) as a pale yellow oil.

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationfiltered
  3. customto remove an insoluble portion, which
  4. washwas washed with water and N,N-dimethylformamide in this order
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customto give a residue
  7. customto partition
  8. extractionThe aqueous layer was extracted with ethyl acetate
  9. washThe combined organic layer was washed with water and brine in this order
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated under a reduced pressure
  12. customto give a residue, which
  13. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent
  14. additionFractions containing the target compound
  15. concentrationwere concentrated

出典と根拠

ORDレコード
ord-c0b08ddcccc8474eb500e72b20d583b8
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

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