Hydrochloric Acid → 3-{5-[2-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-indol-1-yl}-hexanoic acid

HRID 24000Notes

Reaction equation

HRID 24000 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:34])[CH2:7][CH:8]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH2:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[CH2:30][CH2:29][CH2:28][NH:27][C:26]=4[N:25]=3)=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)[CH2:9][CH2:10][CH3:11])C.Cl>CO.O>[N:25]1[C:26]2[NH:27][CH2:28][CH2:29][CH2:30][C:31]=2[CH:32]=[CH:33][C:24]=1[CH2:23][CH2:22][O:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([CH:8]([CH2:9][CH2:10][CH3:11])[CH2:7][C:6]([OH:34])=[O:5])[CH:13]=[CH:14]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 674265983-{5-[2-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-indol-1-yl}-hexanoic acid ethyl ester

Product 1

HCID 102231133-{5-[2-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-indol-1-yl}-hexanoic acidYield 28%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Sodium hydroxide (0.01 g, 0.23 mmol) was added to a solution of 3-{5-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-indol-1-yl}-hexanoic acid ethyl ester (0.02 g, 0.04 mmol) in methanol/water (9/1, 1 mL) and stirred overnight. The reaction was acidified to pH 6 with 1N HCl and the crude product was extracted with ethyl acetate (3×10 mL) and concentrated. The residue was purified by flash chromatography on silica gel (10% methanol in ethyl acetate) to give the title compound (28% yield). 1H NMR (CDCl3) δ 10.4 (bs, 1H), 7.38 (d, 1H, J=8.0 Hz), 7.21 (d, 1H, J=3.2 Hz), 7.14 (d, 1H, J=8.0 Hz), 7.00 (d, 1H, J=2.3 Hz), 6.73 (m, 1H), 6.48 (d, 1H, J=7.3 Hz), 6.32 (d, 2H, J=3.0 Hz), 4.80 (s, 1H), 4.22 (t, 2H, J=7.0 Hz), 3.47 (m, 2H), 2.95 (t, 2H, J=6.8 Hz), 2.68 (m, 4H), 1.88 (m, 4H), 1.15 (m, 2H), 0.81 (t, 3H, J=7.4 Hz). Mass Spectrum (LCMS, ESI) calculated for C24H30N3O3 408.2 (M+H); found 408.3.

Workup

  1. extractionthe crude product was extracted with ethyl acetate (3×10 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on silica gel (10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-9fad862599fd46ca8b6d9973d45e83d0
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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