2,6-Lutidine → HCID 57811389, compound

HRID 885603Notes

Reaction equation

HRID 885603 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].Cl.C(N=C=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1.N1C(C)=CC=CC=1C.[Br:45][C:46]1[N:47]([C:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[C:59]([CH:66]3[CH2:68][CH2:67]3)=[CH:58][CH:57]=2)[C:48]([S:51][CH2:52][C:53](O)=[O:54])=[N:49][N:50]=1>ClCCl>[Br:45][C:46]1[N:47]([C:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[C:59]([CH:66]3[CH2:68][CH2:67]3)=[CH:58][CH:57]=2)[C:48]([S:51][CH2:52][C:53]([NH:6][CH:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH3:2])=[O:14])=[O:54])=[N:49][N:50]=1

Participants

7

Reactant 5

HCID 79372,6-LutidineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53465279Lesinurad

Product 1

HCID 57811389HCID 57811389, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylalanine methyl ester hydrochloride (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 purified by SGC (0-100% EtOAc/Hexanes).

Workup

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

Sources & evidence

ORD record
ord-40341f5fc78d4ab49c6fb47cfdbf13c1
Source dataset
uspto-grants-2012_08
Patent number
US08242154B2

Reaction notes

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