Acetyl chloride → 1-(3-(3-(2,4-Difluorophenyl)-4-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazol-1-yl)pyrrolidin-1-yl)ethanone

HRID 1929997ノート

反応式

HRID 1929997 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=3)[N:19]=2)=[CH:12][N:11]([CH:26]2[CH2:30][CH2:29][NH:28][CH2:27]2)[N:10]=1.CCN(C(C)C)C(C)C.[C:40](Cl)(=[O:42])[CH3:41]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH:23]([CH3:24])[CH3:25])=[N:21][N:22]=3)[N:19]=2)=[CH:12][N:11]([CH:26]2[CH2:30][CH2:29][N:28]([C:40](=[O:42])[CH3:41])[CH2:27]2)[N:10]=1

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 579298656-(3-(2,4-Difluorophenyl)-1-(pyrrolidin-3-yl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine

生成物 1

HCID 579299381-(3-(3-(2,4-Difluorophenyl)-4-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazol-1-yl)pyrrolidin-1-yl)ethanone収率 84.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a round bottom flask was added 6-(3-(2,4-difluorophenyl)-1-(pyrrolidin-3-yl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine (0.150 g, 0.366 mmol, Example #Q.1.1.1), DCM (10 mL), DIPEA (0.077 mL, 0.440 mmol) and acetyl chloride (0.029 mL, 0.403 mmol). The reaction mixture was stirred at ambient temperature for about 10 min. The reaction mixture was diluted with DCM (50 mL) and washed with saturated aqueous NaHCO3 (50 mL), dried with MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (40 g RediSep® silica gel; DCM/MeOH gradient from 1:0 to 9:1) to give the title compound (0.140 g, 84%): LC/MS (Table 1, Method g) Rt=2.07 min; MS m/z: 452.4 (M+H)+.

後処理

  1. washwashed with saturated aqueous NaHCO3 (50 mL)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (40 g RediSep® silica gel; DCM/MeOH gradient from 1:0 to 9:1)

出典と根拠

ORDレコード
ord-f9efffe579174a81bcb19f4e80129da1
出典データセット
uspto-grants-2012_05
特許番号
US08188083B2

反応ノート

読み込み中…