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

HRID 1467097Notes

Reaction equation

HRID 1467097 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][CH2:27][O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][C:30]=1[O:38][CH3:39]>>[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:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:29]([O:28][CH2:27][CH2:26][CH2:25][OH:24])=[C:30]([O:38][CH3:39])[CH:31]=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 105611914-(3-Hydroxypropoxy)-3-methoxybenzoic acidHCID 86658218(S)-ethyl 4-amino-5-(2-aminobutoxy)-2-methylquinoline-3-carboxylate

Product 1

HCID 86658222(S)-ethyl 4-amino-5-(2-(4-(3-hydroxypropoxy)-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-(3-hydroxypropoxy)-3-methoxybenzoic acid (Baraldi, P. G. et al. J. Med. Chem. 1999, 42, 5131.) as brown solid (41%). MS 526 (MH+).

Sources & evidence

ORD record
ord-f584d4874877402ea34adf72f6cf5ecb
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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