Sodium Hydroxide → 2-Methyl-3-{5-[3-(2-pyridylamino)propoxy]indolyl}propanoic acid

HRID 23981Notes

Reaction equation

HRID 23981 reaction equation
[CH3:1][CH:2]([CH2:7][C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)=[CH:12][CH:11]=2)[C:3]([O:5]C)=[O:4].[OH-].[Na+]>CO.O>[CH3:1][CH:2]([CH2:7][C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)=[CH:12][CH:11]=2)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22570378HCID 22570378, compound

Product 1

HCID 225703032-Methyl-3-{5-[3-(2-pyridylamino)propoxy]indolyl}propanoic acidYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-methyl-3-{5-[3-(2-pyridylamino)propoxy]indolyl}propanoate (0.015 g, 0.04 mmol), as prepared in the preceding step, in methanol (5.0 mL) was added a solution of NaOH (0.1 g, 2.5 mmol) in H2O (0.3 mL), and the reaction was stirred at ambient temperature overnight. After evaporating the solvent in vacuo, the residue is taken up in H2O (5 mL) and acidified to pH 4-5 with 10% HCl and extracted with ethyl acetate (2×15 ML). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel (4% methanol in methylene chloride) to give the title compound as an oil (0.011 g, 80%). 1H-NMR (400 MHz, CDCl3) δ 7.86 (d, J=5.6 Hz, 1H), 7.50 (m, 1H), 7.26 (d, J=8.9 Hz, 1H), 7.07 (dd, J=13.1, 2.8 Hz, 2H), 6.84 (dd, J=8.9, 2.4 Hz, 1H), 6.56 (m, 2H), 6.32 (d, J=2.0 Hz, 1H), 4.38 (dd, J=14.3, 7.0 Hz, 1H), 4.07 (t, J=5.8 Hz, 2H), 4.01 (dd, J=14.3, 7.5 Hz, 1H), 3.44 (t, J=6.7 Hz, 2H), 2.92 (q, J=7.1 Hz, 1H), 2.08 (m, 2H), 1.12 (d, J=7.1 Hz, 3H). Mass spectrum (LCMS, ESI pos.) Calcd. for C20H23N3O3 354.3 (M+H); Found: 354.2.

Workup

  1. customAfter evaporating the solvent in vacuo
  2. extractionextracted with ethyl acetate (2×15 ML)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (4% methanol in methylene chloride)

Sources & evidence

ORD record
ord-cd9590110ebd459f9694ca3f1d48c8bd
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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