Hydrochloric Acid → 2-Chloro-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]-pyridine-3,5-dicarbonitrile

HRID 1913504Notes

Reaction equation

N(OCCC(C)C)=O.N[C:10]1[C:15]([C:16]#[N:17])=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][OH:27])=[CH:20][CH:19]=2)[C:13]([C:28]#[N:29])=[C:12]([O:30][CH2:31][C:32]2[N:33]=[C:34]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)[O:35][CH:36]=2)[N:11]=1.[ClH:44]>C(#N)C.[Cu](Cl)Cl>[Cl:44][C:10]1[C:15]([C:16]#[N:17])=[C:14]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][OH:27])=[CH:22][CH:23]=2)[C:13]([C:28]#[N:29])=[C:12]([O:30][CH2:31][C:32]2[N:33]=[C:34]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)[O:35][CH:36]=2)[N:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

78 mg (0.67 mmol) of isopentyl nitrite and 90 mg (0.67 mmol) of copper(II) chloride were initially charged in 8.5 ml of acetonitrile, and 72 mg (0.64 mmol) of the compound from Example 49A were added. The reaction mixture was stirred at 60° C. for 3 h. 8.5 ml of 1N hydrochloric acid were added to the reaction solution. The aqueous phase was extracted twice with in each case 20 ml of ethyl acetate, and the combined organic phases were dried over magnesium sulfate. After removal of the solvent on a rotary evaporator, the residue was dried under reduced pressure and used without further purification for the subsequent reaction.

Workup

extractionThe aqueous phase was extracted twice with in each case 20 ml of ethyl acetate
dry with materialthe combined organic phases were dried over magnesium sulfate
customAfter removal of the solvent
customon a rotary evaporator
customthe residue was dried under reduced pressure
customused without further purification for the subsequent reaction

Sources & evidence

ORD record: ord-3632816299e44feab97006dcef0a7cfe
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609686B2

Reaction notes

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