Phosgene → rac-(4S*,5R*)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

HRID 1894321Notes

Reaction equation

HRID 1894321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:34])[C@:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[NH:11][C:10]([C:21]3[C:22]([O:31][CH2:32][CH3:33])=[CH:23][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[N:25][CH:26]=3)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:42](Cl)([Cl:44])=[O:43]>C(Cl)Cl.C1(C)C=CC=CC=1>[C:27]([C:24]1[N:25]=[CH:26][C:21]([C:10]2[N:11]([C:42]([Cl:44])=[O:43])[C:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([CH3:34])[N:9]=2)=[C:22]([O:31][CH2:32][CH3:33])[CH:23]=1)([CH3:28])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 67205372HCID 67205372, compound

Product 1

HCID 76588499rac-(4S*,5R*)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-2-tert-butyl-4-ethoxy-pyridine (20 mg) and triethylamine (200 uL, 1.43 mmol) in 5 mL of methylene chloride at 0° C. was added 0.3 mL of 1.9 M phosgene in toluene solution (Fluka). After stirring for 30 min the mixture was taken up in methylene chloride and washed with water, dried over anhydrous sodium sulfate, filtered and concentrated to give rac-(4S*,5R*)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride as a white solid (22 mg). It was used in the next reaction without purification

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ede6e9f358c049fa9f9bb1ead1c82f6c
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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