Triethylamine → HCID 25261976, compound

HRID 1894322Notes

Reaction equation

HRID 1894322 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(=[O:4])=[O:3].C(N(CC)CC)C.[C:21]([C:25]1[N:30]=[CH:29][C:28]([C:31]2[N:32]([C:52](Cl)=[O:53])[C:33]([C:45]3[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=3)([CH3:44])[C:34]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)([CH3:36])[N:35]=2)=[C:27]([O:55][CH2:56][CH3:57])[CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl>[C:21]([C:25]1[N:30]=[CH:29][C:28]([C:31]2[N:32]([C:52]([N:11]3[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH2:9][CH2:10]3)=[O:53])[C@@:33]([C:45]3[CH:46]=[CH:47][C:48]([Cl:51])=[CH:49][CH:50]=3)([CH3:44])[C@@:34]([C:37]3[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=3)([CH3:36])[N:35]=2)=[C:27]([O:55][CH2:56][CH3:57])[CH:26]=1)([CH3:22])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 498534781-(3-(Methylsulfonyl)propyl)piperazineHCID 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

Product 1

HCID 25261976HCID 25261976, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

1-(3-Methanesulfonyl-propyl)-piperazine (30 mg, 0.11 mmol, prepared as described in Fotouhi, N. et al. WO 2005110996) was suspended in 5 mL of methylene chloride and cooled to 0° C. Triethylamine was added followed by drop wise addition of 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 in 2 mL of methylene chloride. The mixture was stirred at room temperature for 30 min and then taken up in methylene chloride and washed successively with 10% sodium hydrogen carbonate and water. The methylene chloride phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography on silica gel eluting with methylene chloride/methanol (95:5) gave rac-[(4S*,5R*)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-[4-(3-methanesulfonyl-propyl)-piperazin-1-yl]-methanone as a white solid (16 mg). HR-MS (ES, m/z) calculated for C37H48N5O4SCl2 [(M+H)+] 728.2799, observed 728.2793.

Workup

  1. washwashed successively with 10% sodium hydrogen carbonate and water
  2. dry with materialThe methylene chloride phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography on silica gel eluting with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-2efdac802b914aea8067a366790704c1
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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