4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride → methyl (S)-2-[4-(4-fluorobenzyl)piperazin-1-yl]-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl-amino]propanoate

HRID 472137Notes

Reaction equation

HRID 472137 reaction equation
Cl.Cl.Cl.[NH2:4][CH2:5][C@H:6]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)[C:7]([O:9][CH3:10])=[O:8].Cl.[CH3:26][C:27]1[CH:36]=[C:35]([CH2:37][O:38][C:39]2[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=2)[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1>>[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:14]2[CH2:13][CH2:12][N:11]([C@@H:6]([CH2:5][NH:4][S:45]([C:42]3[CH:43]=[CH:44][C:39]([O:38][CH2:37][C:35]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=[C:27]([CH3:26])[CH:36]=4)=[CH:40][CH:41]=3)(=[O:46])=[O:47])[C:7]([O:9][CH3:10])=[O:8])[CH2:16][CH2:15]2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochlorideHCID 86667914methyl (S)-3-amino-2-[4-(4-fluorobenzyl)piperazin-1-yl]propanoate trihydrochloride

Product 1

HCID 86675023methyl (S)-2-[4-(4-fluorobenzyl)piperazin-1-yl]-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl-amino]propanoateYield 46%

Procedure

In a manner analogous to example 3.6, using 1.5 g (3.7 mmol) of methyl (S)-3-amino-2-[4-(4-fluorobenzyl)piperazin-1-yl]propanoate trihydrochloride and 1.6 g (4.1 mmol) of 4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride (prepared as described in 17.2), 1.0 g (46%) of methyl (S)-2-[4-(4-fluorobenzyl)piperazin-1-yl]-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propanoate is obtained in the form of a white solid.

Sources & evidence

ORD record
ord-126df8096cef4216a339b0f4c1f5c691
Source dataset
uspto-grants-2014_01
Patent number
US08633196B2

Reaction notes

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