Dimethylformamide → HCID 22612408, compound

HRID 844077Notes

Reaction equation

HRID 844077 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[C:6](COC3N=CC=CC=3C(O)=O)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([OH:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=1.[OH2:34].O[N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44]C=2N=N1.Cl.C(N=C=N)C.CN(C)[CH:53]=[O:54]>O>[OH:33][C:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:53](=[O:54])[C:41]2[CH:42]=[CH:43][CH:44]=[N:36][C:40]=2[O:34][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH2:4][CH2:3][C:2]3=[O:1])=[CH:25][CH:26]=1)([CH3:31])[CH3:32]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 27960291-Hydroxybenzotriazole hydrateHCID 101542112-[4-(Aminomethyl)phenyl]propan-2-olHCID 21883477Ethylcarbodiimide hydrochlorideHCID 54463944HCID 54463944, compound

Product 1

HCID 22612408HCID 22612408, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(1-Oxo-indan-4-ylmethoxy)-nicotinic acid (0.220 grams, 0.818 mmole), 2-(4-Aminomethyl-phenyl)-propan-2-ol (0.128 grams, 0.779 mmole), and 1-hydroxybenzotriazole hydrate (0.116 grams, 0.857 mmole) in dry dimethylformamide (30 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.1795 grams, 0.935 mmole) and stirred over night. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to give an oil that was purified by chromatography on silica eluting with 60% ethyl acetate/hexane to give a yellow solid. (0.078 g). M.P. 145-147° C.; Anal. calcd. for C25H24N2O4: C, 72.10; H, 5.81; N, 6.73. Found: C, 71.79; H, 5.67; N, 6.61.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas purified by chromatography on silica eluting with 60% ethyl acetate/hexane
  8. customto give a yellow solid

Sources & evidence

ORD record
ord-492cf24f66c44760901f24a006b380fc
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

Loading…