Dimethylformamide → 5-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 2250443노트

반응식

HRID 2250443 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([OH:17])=O)[NH:12][C:9]2=[CH:10][N:11]=1.Cl.Cl.[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)([CH3:22])[CH3:21].CN(C=O)C.CCN(C(C)C)C(C)C>>[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:15]([C:13]2[NH:12][C:9]3=[CH:10][N:11]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=[C:8]3[CH:14]=2)=[O:17])[CH2:25][CH2:24]1)([CH3:22])[CH3:21]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 177503401-(Propan-2-yl)piperidin-4-amine dihydrochlorideHCID 692283985-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

생성물 1

HCID 865958665-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

실험 절차

To a solution of 820 mg (3.47 mmol) of 5-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid and 745 mg (3.47 mmol) 1-isopropyl-piperidin-4-ylamine dihydrochloride in 30 mL absolute DMF 1.13 g (3.47 mmol) TOTU and 1.81 mL (10.41 mmol) DIPEA were added and the mixture was stirred for 4 h at room temperature. The solvent was removed in vacuo, the residue dissolved in CH2Cl2 and the CH2Cl2 phase washed with a saturated NaHCO3 solution. The organic phase was concentrated and the residue purified by chromatography over silica gel using CH2Cl2/MeOH/HOAc/H2O=90/10/1/1 as eluent. The fractions containing the product were combined and concentrated. The residue was dissolved in CH2Cl2 and the CH2Cl2 phase was washed with a saturated NaHCO3 solution. The phases were separated and the organic phase dried over Na2SO4. After filtration the solvent was removed in vacuo. Yield: 461 mg.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in CH2Cl2
  3. washthe CH2Cl2 phase washed with a saturated NaHCO3 solution
  4. concentrationThe organic phase was concentrated
  5. customthe residue purified by chromatography over silica gel
  6. additionThe fractions containing the product
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in CH2Cl2
  9. washthe CH2Cl2 phase was washed with a saturated NaHCO3 solution
  10. customThe phases were separated
  11. dry with materialthe organic phase dried over Na2SO4
  12. filtrationAfter filtration the solvent
  13. customwas removed in vacuo

출처 및 근거

ORD 기록
ord-d9ad0c3f68534bbdb3b8e8c7ddd2b3d9
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07317027B2

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