Acetyl chloride → N-(1-cyclopropyl-4-iodo-1H-pyrazol-5-yl)acetamide

HRID 1051687Notes

Reaction equation

[CH:1]1([N:4]2[C:8]([NH2:9])=[C:7]([I:10])[CH:6]=[N:5]2)[CH2:3][CH2:2]1.C(NC(C)C)(C)C.[C:18](Cl)(=[O:20])[CH3:19]>ClCCl>[CH:1]1([N:4]2[C:8]([NH:9][C:18](=[O:20])[CH3:19])=[C:7]([I:10])[CH:6]=[N:5]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

A 100-mL round-bottom flask was charged with 1-cyclopropyl-4-iodo-1H-pyrazol-5-amine (0.250 g, 1.00 mmol), N,N-diisopropylamine (0.52 mL, 2.99 mmol) and dichloromethane (8 mL), and the solution was cooled to 0° C. A solution of acetyl chloride (0.085 mL, 1.19 mmol) in dichloromethane (2 mL) was added dropwise, and the resulting solution stirred for 1 h at 0° C. The reaction mixture was concentrated under vacuum, and the residue was purified via column chromatography on silica gel (gradient elution with 0.5-50% ethyl acetate/petroleum ether) to afford N-(1-cyclopropyl-4-iodo-1H-pyrazol-5-yl)acetamide (0.300 g, 92%) as yellow oil. MS (ESI, pos. ion) m/z 292 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated under vacuum
customthe residue was purified via column chromatography on silica gel (gradient elution with 0.5-50% ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-67d176aa43d74a0c9477f6497a07001e
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388161B2

Reaction notes

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