Diisopropylethylamine → [4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-(morpholine-4-sulfonyl)-piperazin-1-yl]-methanone

HRID 31512Notes

Reaction equation

HRID 31512 reaction equation
Cl.[N:2]1([S:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]2[CH:37]([C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=3)[N:36]([C:45](Cl)=[O:46])[C:35]([C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][C:49]=3[O:58][CH2:59][CH3:60])=[N:34]2)=[CH:29][CH:28]=1>C(Cl)Cl>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]2[CH:37]([C:38]3[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=3)[N:36]([C:45]([N:5]3[CH2:4][CH2:3][N:2]([S:8]([N:11]4[CH2:12][CH2:13][O:14][CH2:15][CH2:16]4)(=[O:10])=[O:9])[CH2:7][CH2:6]3)=[O:46])[C:35]([C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:55])([F:56])[F:57])=[CH:50][C:49]=3[O:58][CH2:59][CH3:60])=[N:34]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 42883596813463-32-0HCID 597928204,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride

Product 1

HCID 11331631[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-(morpholine-4-sulfonyl)-piperazin-1-yl]-methanoneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(Piperazine-1-sulfonyl)-morpholine hydrochloride (0.042 mmol) was suspended in methylene chloride, and 400 uL of diisopropylethylamine was added. The mixture was added to 4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride (10 mg, 0.019 mmol, example 3), and the reaction mixture was allowed to stand overnight. It was diluted with methylene chloride and washed with water. The organic layer was evaporated, and the residue purified by flash chromatography using ethyl acetate and hexanes to give [4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-(morpholine-4-sulfonyl)-piperazin-1-yl]-methanone (9.0 mg). LR-MS: 740.2 [(M+H)+].

Workup

  1. washwashed with water
  2. customThe organic layer was evaporated
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-68e972d2171d432ba1d7f375ca42e363
Source dataset
uspto-grants-2008_09
Patent number
US07425638B2

Reaction notes

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