Trifluoroacetic acid → 4-(5-(6-Amino-pyridin-3-yl)-isoxazol-3-ylmethyl)-phenol

HRID 640468ノート

反応式

HRID 640468 の反応式
FC(F)(F)C(O)=O.C([O:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][C:21]2[CH:25]=[C:24]([C:26]3[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=3)[O:23][N:22]=2)=[CH:18][CH:17]=1)C1C=CC=CC=1.C1(SC)C=CC=CC=1.C(=O)([O-])O.[Na+]>O>[NH2:32][C:29]1[N:30]=[CH:31][C:26]([C:24]2[O:23][N:22]=[C:21]([CH2:20][C:19]3[CH:33]=[CH:34][C:16]([OH:15])=[CH:17][CH:18]=3)[CH:25]=2)=[CH:27][CH:28]=1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 516892Sodium BicarbonateHCID 592554535-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine

生成物 1

HCID 592554134-(5-(6-Amino-pyridin-3-yl)-isoxazol-3-ylmethyl)-phenol収率 74.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a trifluoroacetic acid (5 mL) solution of 5-(3-(4-benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine (270 mg, 0.755 mmol) described in Example 28 was added thioanisole (355 μL, 3.02 mmol) at 0° C., which was stirred for 1 hour and 20 minutes at room temperature. Sodium hydrogencarbonate and water were added to the reaction mixture at 0° C., which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (150 mg, 74%).

後処理

  1. extractionwhich was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1)

出典と根拠

ORDレコード
ord-8aed46ce38d44716abff4b90ad0cf1bf
出典データセット
uspto-grants-2010_04
特許番号
US07691882B2

反応ノート

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