Ammonium Chloride → HCID 11659501, compound

HRID 1982899Notes

Reaction equation

C(OC(=O)[N:7]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[N+:14]([O-])=O)(C)(C)C.[CH3:26][C:27]([Mg]Br)=[CH:28][CH3:29].[Cl-:32].[NH4+]>O1CCCC1>[ClH:32].[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][NH:7][C:8]2[C:13]3[NH:14][C:28]([CH3:29])=[C:27]([CH3:26])[C:12]=3[CH:11]=[N:10][CH:9]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: -20 °C

Procedure

(4-Fluorobenzyl)-(4-nitropyridin-3-yl)-carbamic acid tert-butyl ester (5.1 g) prepared in Step 2 was dissolved in anhydrous tetrahydrofuran (100 ml) under a nitrogen atmosphere. 1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution, 55.0 ml, 65.2 mmol) was added at −78° C. to the solution, which was then stirred for 5 hours at −20° C. 20 ml of 20% ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate (200 ml) twice. The separated organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/methanol=10/1 (v/v)), dissolved in 1 ml of ethyl acetate and then saturated with hydrochloric acid gas. The resulting precipitate was filtered to give the titled compound as a pale yellow solid (2.1 g, 35.0%).

Workup

extractionwas then extracted with ethyl acetate (200 ml) twice
dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/methanol=10/1 (v/v))
dissolutiondissolved in 1 ml of ethyl acetate
filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record: ord-74cfddbc8c554fadb9041791e023f1e1
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541366B2

Reaction notes

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