Triethylamine → HCID 17754544, compound

HRID 2263953Notes

Reaction equation

HRID 2263953 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:35])[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[N:11]([C:21](Cl)=[O:22])[C:10]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:25]=3[O:32][CH2:33][CH3:34])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:43][S:44]([CH2:47][CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)(=[O:46])=[O:45]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]2([CH3:35])[C@:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[N:11]([C:21]([N:53]3[CH2:54][CH2:55][N:50]([CH2:49][CH2:48][CH2:47][S:44]([CH3:43])(=[O:45])=[O:46])[CH2:51][CH2:52]3)=[O:22])[C:10]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:25]=3[O:32][CH2:33][CH3:34])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 498534781-(3-(Methylsulfonyl)propyl)piperazineHCID 86612880HCID 86612880, compound

Product 1

HCID 17754544HCID 17754544, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-(4-cyano-2-ethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (˜175 mg, 0.26 mmol) in dichloromethane (10 mL) and triethylamine (0.35 g, 3.34 mmol) at 0° C. was treated with 1-(3-methanesulfonylpropyl)piperazine (0.11 g, 0.39 mmol, prepared as described in Fotouhi, N. et a. WO 2005110996) for 0.5 h. The reaction was washed with cold water, dried over anhydrous magnesium sulfate, filtered and evaporated to give a solid. Trituration with ether and filtration gave the title compound as a racemic mixture. The enantiomers were then separated by supercritical fluid chromatography (Berger Instrument Multi-Gram II, Daicel ChiralPak OD-H 3×25 cm, 35° C. at 100 bar, eluting with 35% methanol in carbon dioxide). HR-MS (ES, m/z) calculated for C35H40N5O4SCl2 [(M+H)+] 696.2173, observed 696.2167.

Workup

  1. customprepared
  2. washThe reaction was washed with cold water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a solid
  7. filtrationTrituration with ether and filtration

Sources & evidence

ORD record
ord-385a6e8fe3104a46bcfdacdd63e794a3
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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