Diisopropylethylamine → [5-(4-Fluoro-phenyl)-2-(3-methoxy-2-triisopropylsilanyloxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone

HRID 1046925Notes

Reaction equation

HRID 1046925 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=3[O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[NH:10][N:9]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[F:41][C:42]1[CH:50]=[C:49]([F:51])[CH:48]=[C:47]([F:52])[C:43]=1[C:44](Cl)=[O:45]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=3[O:21][Si:22]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:29]([CH3:31])[CH3:30])[N:10]([C:44]([C:43]3[C:47]([F:52])=[CH:48][C:49]([F:51])=[CH:50][C:42]=3[F:41])=[O:45])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 672795175-(4-Fluoro-phenyl)-2-(3-methoxy-2-triisopropylsilanyloxy-phenyl)-2,3-dihydro-[1,3,4]thiadiazole

Product 1

HCID 67279689[5-(4-Fluoro-phenyl)-2-(3-methoxy-2-triisopropylsilanyloxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone

Procedure

To the solution of 5-(4-fluoro-phenyl)-2-(3-methoxy-2-triisopropylsilanyloxy-phenyl)-2,3-dihydro-[1,3,4]thiadiazole is added DIEA (3.09 mmol) and 2,4,6-tri-fluorobenzoyl chloride (3.09 mmol) and the reaction mixture is stirred for 12 hours at room temperature. After concentration, the residue is purified by automated column chromatography (hexane/EtOAc) to yield [5-(4-fluoro-phenyl)-2-(3-methoxy-2-triisopropylsilanyloxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone.

Workup

  1. concentrationAfter concentration
  2. customthe residue is purified by automated column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-aa4ef77088f24776988d3c7f7ce28279
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

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