4-(3-Hydroxypropoxy)-3-methoxybenzoic acid → (S)-ethyl 4-amino-5-(2-(4-(3-hydroxypropoxy)-3-methoxybenzamido)propoxy)-2-methylquinoline-3-carboxylate

HRID 2047813Notes

Reaction equation

HRID 2047813 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]([NH2:16])[CH3:15])[N:5]=[C:4]([CH3:17])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH:23][CH2:24][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:16][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][C:28]([O:27][CH2:26][CH2:25][CH2:24][OH:23])=[C:29]([O:37][CH3:38])[CH:30]=2)[CH3:15])[N:5]=[C:4]([CH3:17])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

3

Reactant 2

HCID 105611914-(3-Hydroxypropoxy)-3-methoxybenzoic acidHCID 86658188(S)-ethyl 4-amino-5-(2-aminopropoxy)-2-methylquinoline-3-carboxylate

Product 1

HCID 86658197(S)-ethyl 4-amino-5-(2-(4-(3-hydroxypropoxy)-3-methoxybenzamido)propoxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 24a from (S)-ethyl 4-amino-5-(2-aminopropoxy)-2-methylquinoline-3-carboxylate (Example 26b) and 4-(3-hydroxypropoxy)-3-methoxybenzoic acid (Baraldi, P. G. et al. J. Med. Chem. 1999, 42, 5131) as a brown solid. MS 512 (MH+).

Sources & evidence

ORD record
ord-bafe586f5a1c472a92ab33c8de329f81
Source dataset
uspto-grants-2013_11
Patent number
US08592592B2

Reaction notes

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