Hydrochloric Acid → HCID 68870405, compound

HRID 2105879Notes

Reaction equation

HRID 2105879 reaction equation
[N:1]1([C:7](=[O:15])[CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C@H:32]2[C@@H:36]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)[N:35]([C:44](Cl)=[O:45])[C:34]([C:47]3[CH:52]=[CH:51][C:50]([C:53]#[N:54])=[CH:49][C:48]=3[O:55][CH2:56][CH3:57])=[N:33]2)=[CH:28][CH:27]=1.Cl>C(Cl)Cl.O>[ClH:25].[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C@H:32]2[C@@H:36]([C:37]3[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=3)[N:35]([C:44]([N:12]3[CH2:11][CH2:10][N:9]([CH2:8][C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[O:15])[CH2:14][CH2:13]3)=[O:45])[C:34]([C:47]3[CH:52]=[CH:51][C:50]([C:53]#[N:54])=[CH:49][C:48]=3[O:55][CH2:56][CH3:57])=[N:33]2)=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 1006221-(Morpholinocarbonylmethyl)piperazineHCID 57809160HCID 57809160, compound

Product 1

HCID 68870405HCID 68870405, compoundYield 191%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of morpholin-4-yl-2-piperazin-1-yl-ethanone (17 mg, 0.081 mmol, Oakwood Products) and diisopropylethylamine (10 mg, 0.077 mmol) in 0.5 mL of methylene chloride was added to a solution of (4S,5R)-4,5-bis-(4-chloro-phenyl)-2-(4-cyano-2-ethoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride (35 mg, 0.070 mmol, example 29) in 0.5 mL of methylene in a 4-mL vial. The vial was then capped and shaken for 1 h at room temperature. The reaction mixture was diluted with 1 mL of methylene chloride and 1 mL of water. The vial was agitated and centrifuged. The organic layer was transferred to a 4-mL vial and concentrated in vacuo. The crude was dissolved in 0.5 mL of acetonitrile, and then 0.6 mL of water and 0.492 mL of 0.5 M hydrochloric acid (2.46 mmol) were added to the sample. The sample was frozen with liquid nitrogen and lyophilized to give 4-{(4S,5R)-4,5-bis-(4-chloro-phenyl)-1-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-benzonitrile hydrochloride (47.6 mg, 91% yield). LC-MS: 675.3 [(M+H)+].

Workup

  1. customThe vial was then capped
  2. stirringThe vial was agitated
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude was dissolved in 0.5 mL of acetonitrile
  5. temperatureThe sample was frozen with liquid nitrogen

Sources & evidence

ORD record
ord-5c9089319cff417593f8c2865fc7e103
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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