4-(2-Hydroxyethoxy)-3-methoxybenzoic acid → (S)-ethyl 4-amino-5-(2-(4-(2-hydroxyethoxy)-3-methoxybenzamido)butoxy)-2-methylquinoline-3-carboxylate

HRID 2047836Notes

Reaction equation

HRID 2047836 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][C@@H:14]([NH2:17])[CH2:15][CH3:16])[N:5]=[C:4]([CH3:18])[C:3]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[OH:24][CH2:25][CH2:26][O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][C:29]=1[O:37][CH3:38]>>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][C@@H:14]([NH:17][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][C:28]([O:27][CH2:26][CH2:25][OH:24])=[C:29]([O:37][CH3:38])[CH:30]=2)[CH2:15][CH3:16])[N:5]=[C:4]([CH3:18])[C:3]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

3

Reactant 2

HCID 246940694-(2-Hydroxyethoxy)-3-methoxybenzoic acidHCID 86658218(S)-ethyl 4-amino-5-(2-aminobutoxy)-2-methylquinoline-3-carboxylate

Product 1

HCID 86658220(S)-ethyl 4-amino-5-(2-(4-(2-hydroxyethoxy)-3-methoxybenzamido)butoxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 24a from (S)-ethyl 4-amino-5-(2-aminobutoxy)-2-methylquinoline-3-carboxylate (Example 97b) and 4-(2-hydroxyethoxy)-3-methoxybenzoic acid (Uto, Y. et al. Bioorg. Med. Chem. Lett. 2009, 19, 4151) as brown solid (38%). MS 512 (MH+).

Sources & evidence

ORD record
ord-213b63faf4fc4304b0e3594eed50a2cc
Source dataset
uspto-grants-2013_11
Patent number
US08592592B2

Reaction notes

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