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

HRID 2169948Notes

Reaction equation

HRID 2169948 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]([NH2:18])[CH:15]([CH3:17])[CH3:16])[N:5]=[C:4]([CH3:19])[C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].[OH:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][C:31]=1[O:39][CH3:40]>>[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:18][C:34](=[O:35])[C:33]2[CH:37]=[CH:38][C:30]([O:29][CH2:28][CH2:27][CH2:26][OH:25])=[C:31]([O:39][CH3:40])[CH:32]=2)[CH:15]([CH3:17])[CH3:16])[N:5]=[C:4]([CH3:19])[C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

3

Reactant 2

HCID 105611914-(3-Hydroxypropoxy)-3-methoxybenzoic acidHCID 86658214(S)-ethyl 4-amino-5-(2-amino-3-methylbutoxy)-2-methylquinoline-3-carboxylate

Product 1

HCID 86658226(S)-ethyl 4-amino-5-(2-(4-(3-hydroxypropoxy)-3-methoxybenzamido)-3-methylbutoxy)-2-methylquinoline-3-carboxylate

Procedure

Prepared as in Example 24a from (S)-ethyl 4-amino-5-(2-amino-3-methylbutoxy)-2-methylquinoline-3-carboxylate (Example 95b) and 4-(3-hydroxypropoxy)-3-methoxybenzoic acid (Baraldi, P. G. et al. J. Med. Chem. 1999, 42, 5131.) as brown solid (29%). MS 540 (MH+).

Sources & evidence

ORD record
ord-5164d28a785942d983ebef23c49effa4
Source dataset
uspto-grants-2015_06
Patent number
US09049878B2

Reaction notes

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