Diethyl Ether → HCID 66747676, compound

HRID 2402083Notes

Reaction equation

[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[S:10][C:11]=2[C:12](N(OC)C)=[O:13])=[CH:4][CH:3]=1.[Li]C.[CH3:28]COCC>C1COCC1>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)[S:10][C:11]=2[C:12](=[O:13])[CH3:28])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 4-(4-chlorobenzyl)-N-methoxy-N-methyl-2-(pyridin-4-yl)thiazole-5-carboxamide (1.79 g, 4.79 mmol) in THF (97 mL) at −20° C. was added a 1.60 M solution of MeLi in ether (4.19 mL, 6.70 mmol). The reaction was stirred for 30 minutes at −20° C. An additional portion of a 1.60 M solution of MeLi in ether (0.838 mL, 1.34 mmol) was added and the reaction was stirred for 30 more minutes at −20° C. The reaction was quenched by adding saturated ammonium chloride (25 mL) followed by water (35 mL). The mixture was extracted with ethyl acetate (2×150 mL) and the combined organic layers were dried, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (EA/DCM=0/100-40/20) to give 1.27 g (81% yield) of the title compound as a light yellow solid. LC/MS (FA) ES+ 329, 331. 1H NMR (300 MHz, CDCl3) δ: 8.75-8.73 (m, 2H), 7.83-7.81 (m, 2H), 7.34-7.31 (m, 2H). 7.26-7.23 (m, 2H), 4.53 (s, 2H), 2.59 (s, 3H).

Workup

stirringthe reaction was stirred for 30 more minutes at −20° C
customThe reaction was quenched
additionby adding saturated ammonium chloride (25 mL)
extractionThe mixture was extracted with ethyl acetate (2×150 mL)
customthe combined organic layers were dried
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (EA/DCM=0/100-40/20)

Sources & evidence

ORD record: ord-8bc206a262474c79bf36f3be59b56a83
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796271B2

Reaction notes

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