Sulfuric Acid → HCID 178439460, compound

HRID 1924315Notes

Reaction equation

COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([CH2:17][N:18]4[CH2:22][CH:21]([CH2:23][CH2:24][CH3:25])[CH2:20][C:19]4=[O:26])=[C:11]3[N:10]=[CH:9]2)=CC=1.C1(OC)C=CC=CC=1.OS(O)(=O)=O.C([O-])(O)=O.[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[N:10]1[C:11]2[C:12](=[N:13][CH:14]=[CH:15][C:16]=2[CH2:17][N:18]2[CH2:22][CH:21]([CH2:23][CH2:24][CH3:25])[CH2:20][C:19]2=[O:26])[NH:8][CH:9]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution containing 1-{[3-(4-methoxybenzyl)-3H-imidazo[4,5-b]pyridin-7-yl]methyl}-4-propylpyrrolidin-2-one x187 (0.6 g), anisole (0.4 ml) and concentrated H2SO4 (0.2 ml) in trifluoroacetic acid (4 ml) is stirred in a flow of argon at 20° C. for 2 h. The homogeneous reaction mixture is added dropwise at 0° C. to a mixture of a saturated aqueous solution of NaHCO3 (50 ml) and ethyl acetate (50 ml). The organic layer is separated. The aqueous one (pH˜8) is subjected to additional extraction with chloroform containing 10% of tert-butanol. The combined organic layers are dried with anhydrous sodium sulfate and evaporated. The residue is purified by chromatography on silicagel (chloroform/methanol) to afford 1-(3H-imidazo[4,5-b]pyridin-7-ylmethyl)-4-propylpyrrolidin-2-one 95 (0.34 g).

Workup

customThe organic layer is separated
extractionThe aqueous one (pH˜8) is subjected to additional extraction with chloroform containing 10% of tert-butanol
dry with materialThe combined organic layers are dried with anhydrous sodium sulfate
customevaporated
customThe residue is purified by chromatography on silicagel (chloroform/methanol)

Sources & evidence

ORD record: ord-ed78d355f1964a9ab81a36f1838439b3
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178533B2

Reaction notes

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