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

HRID 63593노트

반응식

HRID 63593 반응식
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

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 468676602-Amino-4,5-dichloro-3-nitropyridineHCID 755306881-[(5-Methyl-1,2,4-oxadiazol-3-yl)methyl]piperazine hydrochloride

생성물 1

HCID 714814732-Amino-5-chloro-4-(4-(5-methyl-1,2,4-oxadiazol-3-yl)methylpiperazin-1-yl)-3-nitropyridine수율 70.2%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
45 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-ca11d6524ce540f6b793af1492dd8c08
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447092B2

반응 노트

불러오는 중…