Hydrochloric Acid → 4-{[(6-Chloro-3,5-dicyano-4-phenylpyridin-2-yl)thio]methyl}-N-methylpyridine-2-carboxamide

HRID 1500108Notes

Reaction equation

N[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]=1[C:28]#[N:29].N(OCCC(C)C)=O.[ClH:38]>C(#N)C.[Cu](Cl)Cl>[Cl:38][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]=1[C:28]#[N:29]

Participants

Conditions

Temperature: 60 °C

Procedure

1.42 g (3.55 mmol) of the compound from Example 24A are initially charged in 30 ml of acetonitrile, 0.96 ml (7.10 mmol) of isopentyl nitrite and 0.95 g (7.10 mmol) of copper(II) chloride are added and the mixture is stirred at 60° C. for 5 hours. Once more, the same amount of copper(II) chloride is added and the mixture is stirred at 60° C. overnight. 7 ml of 1N hydrochloric acid are added, the mixture is extracted three times with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated. The residue is purified by preparative HPLC (with 0.1% TFA added).

Workup

stirringthe mixture is stirred at 60° C. overnight
extractionthe mixture is extracted three times with ethyl acetate
washthe combined organic phases are washed with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulphate
concentrationconcentrated
customThe residue is purified by preparative HPLC (with 0.1% TFA added)

Sources & evidence

ORD record: ord-802e8d14fcf442c1a1555550314bdb5e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09205077B2

Reaction notes

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