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

HRID 1691291노트

반응식

HRID 1691291 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-fdeee11f54a44eae93dcae34f1756fae
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153662B2

반응 노트

불러오는 중…