4-Methylmorpholine → 2-(4-(1H-pyrazol-1-yl)phenyl)-N,2-dimethoxy-N-methylacetamide

HRID 512597Notes

Reaction equation

C[C:2]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)=[CH:10][CH:9]=1)([O:6][CH3:7])[C:3]([OH:5])=O.CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[CH3:35][NH:36][O:37][CH3:38]>ClCCl.C([O-])(O)=O.[Na+]>[N:14]1([C:11]2[CH:10]=[CH:9][C:8]([CH:2]([O:6][CH3:7])[C:3]([N:36]([O:37][CH3:38])[CH3:35])=[O:5])=[CH:13][CH:12]=2)[CH:18]=[CH:17][CH:16]=[N:15]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetic acid (0.18 g, 0.77 mmol) in dry dichloromethane (5 mL) under argon was added N-methylmorpholine (0.18 mL, 1.7 mmol). The reaction mixture was cooled to 0° C., isobutylchloroformate was added, (0.11 mL, 0.85 mmol) and the mixture was stirred for 40 minutes. N,O-dimethylhydroxylamine hydrochloride (0.098 g, 1 mmol) was then added in one portion and slowly allowed to warm to room temperature and stirred for 18 hours. The mixture was diluted with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-80% EtOAc-hexanes) provided 2-(4-(1H-pyrazol-1-yl)phenyl)-N,2-dimethoxy-N-methylacetamide (0.16 g, 76% yield).

Workup

temperatureto warm to room temperature
stirringstirred for 18 hours
extractionextracted with EtOAc
washThe combined organics were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customPurification by chromatography (0-80% EtOAc-hexanes)

Sources & evidence

ORD record: ord-c42c3d84f2224bd5a5e89ac3aa12c6e4
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102643B2

Reaction notes

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