Diisopropylethylamine → 1-(2-Chloro-4,5-difluorobenzoyl)-3-[4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-2-trifluoromethoxyphenyl]urea

HRID 722223Notes

Reaction equation

HRID 722223 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].Cl.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[NH:27][C:26](=[O:28])[O:25][N:24]=2)=[CH:19][C:18]=1[O:29][C:30]([F:33])([F:32])[F:31].CCN(C(C)C)C(C)C>C(#N)C>[Cl:1][C:2]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:3]=1[C:4]([NH:6][C:7]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[NH:27][C:26](=[O:28])[O:25][N:24]=2)=[CH:19][C:18]=1[O:29][C:30]([F:31])([F:33])[F:32])=[O:8])=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 115575832-Chloro-4,5-difluorobenzoyl IsocyanateHCID 1363606243-(4-amino-3-trifluoromethoxyphenyl)-4H-[1,2,4]-oxadiazol-5-one hydrochloride

Product 1

HCID 1358393801-(2-Chloro-4,5-difluorobenzoyl)-3-[4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-2-trifluoromethoxyphenyl]urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The solution of equivalent amounts of 2-chloro-4,5-difluorobenzoyl isocyanate was added dropwise to the solution of 95 mg of 3-(4-amino-3-trifluoromethoxyphenyl)-4H-[1,2,4]-oxadiazol-5-one hydrochloride and 0.054 ml of Hünig's base in 4 ml of acetonitrile and the mixture was stirred at room temperature for 30 minutes. The solid was then filtered off with suction and dried under reduced pressure.

Workup

  1. filtrationThe solid was then filtered off with suction
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-bda9be1197be4eee9cefc5dc220225ec
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Reaction notes

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