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

HRID 2250443Notes

Reaction equation

HRID 2250443 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d9ad0c3f68534bbdb3b8e8c7ddd2b3d9
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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