Hydrochloric Acid → 2-Chloro-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}thio)-4-(4-{[(2S)-2,3-dihydroxypropyl]oxy}phenyl)pyridine-3,5-dicarbonitrile

HRID 1913495

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][C@@H:26]([OH:29])[CH2:27][OH:28])=[CH:20][CH:19]=2)[C:13]([C:30]#[N:31])=[C:12]([S:32][CH2:33][C:34]2[N:35]=[C:36]([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=3)[O:37][CH:38]=2)[N:11]=1.[ClH:46]>C(#N)C.[Cu](Cl)Cl>[Cl:46][C:10]1[C:15]([C:16]#[N:17])=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C@@H:26]([OH:29])[CH2:27][OH:28])=[CH:20][CH:19]=2)[C:13]([C:30]#[N:31])=[C:12]([S:32][CH2:33][C:34]2[N:35]=[C:36]([C:39]3[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=3)[O:37][CH:38]=2)[N:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

171 mg (1.46 mmol) of isopentyl nitrite and 196 mg (1.46 mmol) of copper(II) chloride were initially charged in 18 ml of acetonitrile. 389 mg (0.73 mmol) of the compound from Example 40A were added, and the mixture was then stirred at 60° C. for 3 h. After cooling to RT, 20 ml of 1N hydrochloric acid were added. The aqueous phase was extracted twice with in each case 30 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate. The solvent was removed, and the product was then used without further purification for the subsequent reaction.

Workup

temperatureAfter cooling to RT
extractionThe aqueous phase was extracted twice with in each case 30 ml of ethyl acetate
dry with materialThe combined organic phases were dried over magnesium sulfate
customThe solvent was removed
customthe product was then used without further purification for the subsequent reaction

Sources & evidence

ORD record: ord-97c28d61df4f40a1854d3d8eed1ad816
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609686B2

Linked notes

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