Ethyl isocyanate → cis-1-[(Ethylamino)carbonyl]-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-3-carboxylic acid

HRID 736735Notes

Reaction equation

HRID 736735 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][C@H:24]3[CH2:28][NH:27][CH2:26][C@H:25]3[C:29]([OH:31])=[O:30])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:32]([N:34]=[C:35]=[O:36])[CH3:33]>>[CH2:32]([NH:34][C:35]([N:27]1[CH2:28][C@H:24]([NH:23][S:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)=[CH:15][CH:16]=2)(=[O:21])=[O:22])[C@H:25]([C:29]([OH:31])=[O:30])[CH2:26]1)=[O:36])[CH3:33]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 68817812cis-4-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-3-carboxylic acid

Product 1

HCID 68817241cis-1-[(Ethylamino)carbonyl]-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-3-carboxylic acidYield 84.7%

Procedure

According to the procedure of Example 17, Step 3, the reaction of 178 mg of cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-3-carboxylic acid (Example 21, Step 1) and 44 mg of ethyl isocyanate provided 175 mg of cis-1-[(ethylamino)carbonyl]-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-3-carboxylic acid in quantitative yield. MS: 513.2 (M+H)+

Sources & evidence

ORD record
ord-5bac97d433c74044bb37946ad621d293
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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