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 985493노트

반응식

HRID 985493 반응식
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

참가 물질

3

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d87ea9a67fde44fcb6172273a4ab4010
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06872730B2

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