Diisopropylethylamine → 2-Amino-5-chloro-4-(4-(5-methyl-1,2,4-oxadiazol-3-yl)methylpiperazin-1-yl)-3-nitropyridine

HRID 63593

Reaction equation

Cl.[CH3:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[N:4]=1.[NH2:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20](Cl)[C:19]([Cl:26])=[CH:18][N:17]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[NH2:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20]([N:12]2[CH2:11][CH2:10][N:9]([CH2:8][C:5]3[N:4]=[C:3]([CH3:2])[O:7][N:6]=3)[CH2:14][CH2:13]2)[C:19]([Cl:26])=[CH:18][N:17]=1

Participants

Conditions

Temperature: 45 °C

Procedure

1-[(5-Methyl-1,2,4-oxadiazol-3-yl)methyl]piperazine hydrochloride (217 mg, 0.99 mmol) and 2-amino-4,5-dichloro-3-nitropyridine (208 mg, 1.0 mmol) were stirred in 2-propanol (5 mL) and diisopropylethylamine (523 μL, 387 mg, 3.0 mmol) was added. The mixture was stirred and heated at 45° C. for 23 h. The reaction was cooled and the product filtered off and washed with 2-propanol. Drying in vacuum gave the product (246 mg, 69%). 1H-NMR (500 MHz, CDCl3), 2.63 (s, 3H, CH3), 2.77 (br m, 4H, piperazine C—H), 3.29 (m, 4H, piperazine C—H), 3.76 (s, 2H, CH2), 5.27 (s, 2H, NH2), 8.02 (s, 1H, pyridine 6-H).

Workup

temperatureThe reaction was cooled
filtrationthe product filtered off
washwashed with 2-propanol
customDrying in vacuum

Sources & evidence

ORD record: ord-ca11d6524ce540f6b793af1492dd8c08
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447092B2

Linked notes

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