Dimethylamine → 4-{5-[(Dimethylamino)methyl]-1,3,4-oxadiazol-2-yl}-2-(methyloxy)aniline

HRID 419337Notes

Reaction equation

Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([O:17][CH3:18])[CH:9]=2)=[N:6][N:7]=1.[CH3:19][NH:20][CH3:21].C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:19][N:20]([CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([O:17][CH3:18])[CH:9]=2)=[N:6][N:7]=1)[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

To 2-(chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole (0.399 g, 1.48 mmol) in dioxane (10 mL) was added dimethylamine (1.87 mL, 40% weight in H2O, 14.8 mmol). The reaction was heated at 60° C. overnight. The reaction was poured into half saturated NaHCO3, extracted with DCM and EtOAc, dried (MgSO4) and concentrated. The residue was taken up in EtOAc (20 mL) and Pd on carbon was added in one portion. The mixture was stirred at rt under H2 (1 atm.) until complete by TLC. The reaction was filtered through Celite® and concentrated to provide the title compound of step D (0.326 g, 1.32 mmol, 89% over two steps). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.18-2.23 (m, 6H), 3.67-3.72 (m, 2H), 3.76-3.82 (m, 3H), 5.47-5.56 (m, 2H), 6.64-6.72 (m, 1H), 7.25 (d, J=2.0 Hz, 1H), 7.30 (dt, J=8.1, 2.1 Hz, 1H).

Workup

extractionextracted with DCM and EtOAc
dry with materialdried (MgSO4)
concentrationconcentrated
additionPd on carbon was added in one portion
filtrationThe reaction was filtered through Celite®
concentrationconcentrated

Sources & evidence

ORD record: ord-32accc09dc514616b7a46a271dd2feb4
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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