2,6-Lutidine → Methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)hexanoate

HRID 1921733Notes

Reaction equation

HRID 1921733 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][NH2:28])[C:20]([O:22][CH3:23])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1.N1C(C)=CC=CC=1C.[Br:59][C:60]1[N:61]([C:70]2[C:79]3[C:74](=[CH:75][CH:76]=[CH:77][CH:78]=3)[C:73]([CH:80]3[CH2:82][CH2:81]3)=[CH:72][CH:71]=2)[C:62]([S:65][CH2:66][C:67](O)=[O:68])=[N:63][N:64]=1>ClCCl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:67](=[O:68])[CH2:66][S:65][C:62]3[N:61]([C:70]4[C:79]5[C:74](=[CH:75][CH:76]=[CH:77][CH:78]=5)[C:73]([CH:80]5[CH2:82][CH2:81]5)=[CH:72][CH:71]=4)[C:60]([Br:59])=[N:64][N:63]=3)[C:20]([O:22][CH3:23])=[O:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 79372,6-LutidineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17968458Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-aminohexanoateHCID 53465279Lesinurad

Product 1

HCID 57811339Methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-aminohexanoate (N-α-Fmoc-Lysine (NH2)—OMe, 1.48 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.86 mmol), 1-hydroxy-7-azabenzotriazole (1.86 mmol) and 2,6-lutidine (0.43 mL. 3.71 mmol) are added to a solution of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid (0.5 g, 1.24 mmol) in dichloromethane (6.18 mL). The mixture is stirred at room temperature for 18 hours and then is purified by SGC (0-100% EtOAc/Hexanes).

Workup

  1. customis purified by SGC (0-100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-d83ae508f40042b7b0866dfcae6a20b4
Source dataset
uspto-grants-2012_05
Patent number
US08173690B2

Reaction notes

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