Quinolin-3-yl-propynoic acid ethyl ester → 3-Quinolin-3-yl-3-{5-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-indol-1-yl}-propionic acid

HRID 24016Notes

Reaction equation

HRID 24016 reaction equation
C([O:3][C:4](=[O:17])[C:5]#[C:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)C.C(OC([N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([CH2:35][CH2:36][O:37][C:38]3[CH:39]=[C:40]4[C:44](=[CH:45][CH:46]=3)[NH:43][CH:42]=[CH:41]4)[N:33]=2)[CH2:28][CH2:27][CH2:26]1)=O)(C)(C)C>>[N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:7]([CH:6]([N:43]2[C:44]3[C:40](=[CH:39][C:38]([O:37][CH2:36][CH2:35][C:32]4[CH:31]=[CH:30][C:29]5[CH2:28][CH2:27][CH2:26][NH:25][C:34]=5[N:33]=4)=[CH:46][CH:45]=3)[CH:41]=[CH:42]2)[CH2:5][C:4]([OH:3])=[O:17])[CH:8]=1

Participants

3

Reactant 2

HCID 9855974Quinolin-3-yl-propynoic acid ethyl esterHCID 668210837-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 101849983-Quinolin-3-yl-3-{5-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-indol-1-yl}-propionic acidYield 81%

Procedure

The title compound was synthesized from quinolin-3-yl-propynoic acid ethyl ester and 7-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester using the procedure described in Example 16, step (d1), in 81% yield as an E/Z isomeric mixture. 1H NMR (CDCl3) δ 8.90 (m, 1H), 8.14 (m, 1.3H), 8.04 (m, 0.7H), 7.79 (m, 2H), 7.58 (m, 1H), 7.30 (d, 1H, J=7.6 Hz), 7.13 (m, 2H), 6.93 (m, 1.3H), 6.75 (m, 1.7H), 6.63 (d, 0.7H, J=3.2 Hz), 6.53 (d, 0.3H, J=3.2 Hz), 6.38 (s, 0.7H), 6.32 (s, 0.3H), 4.38 (m, 2H), 4.05 (m, 2H), 3.75 (t, 2H, J=6.4 Hz), 3.19 (t, 2H, J=6.4 Hz), 2.72 (t, 2H, J=6.4 Hz), 1.91 (m, 2H), 1.51 (s, 9H), 1.13 (t, 0.9H, J=7.0 Hz), 1.05 (t, 2.1H, J=7.0 Hz).

Sources & evidence

ORD record
ord-6d485797638f4c908ab2fc2cb065c654
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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