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

HRID 1295184Notes

Reaction equation

HRID 1295184 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH:6]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[CH2:28][CH2:27][CH2:26][NH:25][C:24]=4[N:23]=3)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9])C.[OH-].[Na+].Cl>C1COCC1.O>[N:23]1[C:24]2[NH:25][CH2:26][CH2:27][CH2:28][C:29]=2[CH:30]=[CH:31][C:22]=1[CH2:21][CH2:20][CH2:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:32])=[O:3])[CH:11]=[CH:12]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 668215293-{5-[3-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-hexanoic acid ethyl ester

Product 1

HCID 102013233-{5-[3-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-hexanoic acidYield 65%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 3-{5-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-hexanoic acid ethyl ester (83.0 mg, 0.218 mmol) and NaOH (52.0 mg, 1.31 mmol) in THF/H2O (3:1) was stirred at room temperature for 2 days. Aqueous HCl solution (1 N) was added to adjust the pH to 4–5. The crude product was extracted with ethyl acetate, and the combined organic layers were washed with brine and dried over Na2SO4. Removal of solvent gave the crude product, which was purified via column chromatography, eluting with 5% methanol in methylene chloride, to give the title compound (65% yield). 1H NMR (CDCl3) δ 9.35 (br, 1H), 7.42 (d, J=8.1 Hz, 1H) 7.27 (m, H), 7.16–7.20 (m, 2H), 6.95 (d, J=7.9 Hz, 1H), 6.40 (d, J=2.5 Hz, 1H), 6.22 (d, J=7.2 Hz, 1H), 4.91 (br, 1H), 3.40 (m, 2H), 2.56–2.82 (m, 10 H), 1.84–2.05 (m, 6H), 0.86 (m, 3H). Mass Spectrum (LCMS, ESI) calculated for C25H32N3O2 406.3 (M+H); found 406.4.

Workup

  1. extractionThe crude product was extracted with ethyl acetate
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customRemoval of solvent
  5. customgave the crude product, which
  6. customwas purified via column chromatography
  7. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-a302bf70c9d44a0682fbc99632d7cc8c
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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