Diisopropylethylamine → 2-{2-[5-(4-Chloro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-acetamide

HRID 1694339Notes

Reaction equation

HRID 1694339 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=3[O:15][CH2:16][C:17]([NH2:19])=[O:18])[NH:10][N:9]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[F:33][C:34]1[CH:42]=[C:41]([F:43])[CH:40]=[C:39]([F:44])[C:35]=1[C:36](Cl)=[O:37]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][CH:11]([C:13]3[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=3[O:15][CH2:16][C:17]([NH2:19])=[O:18])[N:10]([C:36](=[O:37])[C:35]3[C:39]([F:44])=[CH:40][C:41]([F:43])=[CH:42][C:34]=3[F:33])[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 672793222-(2-(5-(4-Chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenoxy)acetamide

Product 1

HCID 580258312-{2-[5-(4-Chloro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-acetamide

Procedure

To the solution of 2-(2-(5-(4-chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenoxy)acetamide is added DIEA (2.0 mmol) and 2,4,6-tri-fluorobenzoyl chloride (2.0 mmol) and the reaction mixture is stirred for 12 hours at room temperature. After evaporation of the solvent, the residue is purified by automated chromatography (hexane/EtOAc) to give 2-{2-[5-(4-chloro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-acetamide: 1H NMR (400 MHz, CDCl3) δ 7.43 (s, 1H), 7.27 (d, J=8.8, 2H), 7.15 (m, 2H), 7.14 (d, J=8.4 Hz, 2H) 6.99 (bs, 1H), 6.84 (t, J=6.4 Hz, 3H), 6.66 (d, J=8.4 Hz, 1H), 6.53 (t, J=8.0 Hz, 2H), 5.29 (bs, 1H), 4.47 (d, J=1.6 Hz, 2H); LC/MS: (ES+) 506.2 (M+1)+.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue is purified by automated chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-4169ce0426cc4055a283e1fd2f36c27b
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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