Propylenediamine → 6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-aminopropyl)amide

HRID 499177

반응식

HRID 499177 반응식
CO[C:3]([C:5]1[N:6]=[N:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)=[O:4].[CH2:29]([NH2:33])[CH:30]([NH2:32])[CH3:31]>>[NH2:32][CH:30]([CH3:31])[CH2:29][NH:33][C:3]([C:5]1[N:6]=[N:7][C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:26])([F:25])[F:27])[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)=[O:4]

참가 물질

3

반응물 2

HCID 6567PropylenediamineHCID 668495266-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid methyl ester

생성물 1

HCID 866197506-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-aminopropyl)amide수율 85%

반응 조건

온도
140 °C

실험 절차

A mixture of 6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid methyl ester (0.200 g, 0.502 mmol) and propane-1,2-diamine (2 mL) was heated in a sealed tube at 140° C. for 12 hours. The mixture was cooled and concentrated under high vacuum to remove excess amount of propane-1,2-diamine. The residue was purified by column chromatography to afford 6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-aminopropyl)amide (0.188 g, 85%) as a white foam. 1H NMR (300 MHz, MeOH-d4) δ 7.92 (d, J=9.3 Hz, 1H), 7.81 (d, J=7.9 Hz, 1H), 7.78-7.61 (m, 2H), 7.50 (d, J=7.3 Hz, 1H), 7.30 (d, J=9.6 Hz, 1H), 4.00-3.82 (m, 4H), 3.72 (t, J=4.9 Hz, 2H), 3.45-3.23 (m, 5H), 1.10 (d, J=6.3 Hz, 3H). MS (ES+) m/z 437.0 (M+1).

후처리

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under high vacuum
  3. customto remove excess amount of propane-1,2-diamine
  4. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-6474da7619c345c387c072ff02c56b3d
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767677B2

연결된 노트

불러오는 중…