2,6-Lutidine → HCID 57811449, compound

HRID 1921727Notes

Reaction equation

HRID 1921727 reaction equation
Cl.C([O:4][C:5](=[O:8])[CH2:6][NH2:7])C.Cl.C(N=C=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1.N1C(C)=CC=CC=1C.[Br:39][C:40]1[N:41]([C:50]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[C:53]([CH:60]3[CH2:62][CH2:61]3)=[CH:52][CH:51]=2)[C:42]([S:45][CH2:46][C:47](O)=[O:48])=[N:43][N:44]=1>ClCCl>[Br:39][C:40]1[N:41]([C:50]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[C:53]([CH:60]3[CH2:62][CH2:61]3)=[CH:52][CH:51]=2)[C:42]([S:45][CH2:46][C:47]([NH:7][CH2:6][C:5]([OH:4])=[O:8])=[O:48])=[N:43][N:44]=1

Participants

7

Reactant 5

HCID 79372,6-LutidineHCID 181649HOAtHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53465279Lesinurad

Product 1

HCID 57811449HCID 57811449, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Glycine ethyl ester hydrochloride (0.21 g, 1.48 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.36 g, 1.86 mmol), 1-hydroxy-7-azabenzotriazole (0.25 g, 1.86 mmol) and 2,6-lutidine (0.43 mL, 3.71 mmol, 3.0) 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), and the mixture is stirred at room temperature for 18 hours. Purification by SGC (0-100% EtOAc/Hexanes) affords 2-(2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)acetic acid.

Workup

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

Sources & evidence

ORD record
ord-11b21e268c0247238b835700661a9adf
Source dataset
uspto-grants-2012_05
Patent number
US08173690B2

Reaction notes

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