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

HRID 63593

反応式

HRID 63593 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
45 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ca11d6524ce540f6b793af1492dd8c08
出典データセット
uspto-grants-2016_09
特許番号
US09447092B2

関連ノート

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