7-{2-[3-(2-Carboxy-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester → 3-{6-[2-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-benzo[b]thiophen-3-yl}-propionic acid

HRID 985493Notes

Reaction equation

HRID 985493 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]4[C:28]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][S:26][C:25]=4[CH:34]=3)[N:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C>C1COCC1>[N:16]1[C:17]2[NH:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=[CH:14][C:15]=1[CH2:18][CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[C:28]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][S:26][C:25]=2[CH:34]=1

Participants

3

Reactant 1

HCID 695482037-{2-[3-(2-Carboxy-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 225070693-{6-[2-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-benzo[b]thiophen-3-yl}-propionic acidYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-{2-[3-(2-Carboxy-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (168 mg, 0.35 mmol) was dissolved in THF (10 ml). Hydrogen chloride gas was bubbled through the solution until the starting material disappears by TLC. Then the solvent was evaporated under vacuum and the crude was chromatographied over silica gel using 5% methanol/ methylene chloride as solvent to yield 32 mg (24%) of 3-{6-[2-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-benzo[b]thiophen-3-yl}-propionic acid. NMR 1H Cl3CD δ: 7.55 (d, 1H, J=8.7 Hz), 7.25 (m, 2H), 6.93 (s, 1H), 6.88 (dd, 1H, J=2.1, 8.7 Hz), 6.43 (d, 1H, J=7.2 Hz), 4.24 (t, 2H, J=6.1 Hz), 3.45 (m, 2H), 3.10 (m, 4H), 2.71 (m, 4H), 1.88 (m, 2H). Mass Spectrum (LCMS, ESI) calculate for C21H23N2O3S 383.14 (M+H) found: 383.3.

Workup

  1. customHydrogen chloride gas was bubbled through the solution until the starting material
  2. customThen the solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-d87ea9a67fde44fcb6172273a4ab4010
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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