Diisopropylethylamine → HCID 178458651、化合物

HRID 450359ノート

反応式

HRID 450359 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=2)[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][CH:3]=1.Cl.[F:22][C:23]1[CH:24]=[CH:25][C:26]([C@@H:29]([NH2:31])[CH3:30])=[N:27][CH:28]=1.C(N(C(C)C)CC)(C)C>CCCCO.C(OCC)(=O)C>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C@@H:29]([NH:31][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=3)[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][CH:3]=2)[CH3:30])=[N:27][CH:28]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 67123789(S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride2 回HCID 178458609HCID 178458609、化合物2 回

生成物 1

HCID 178458651HCID 178458651、化合物収率 66%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A mixture of 6-chloro-N-(5-isopropoxy-1H-pyrazol-3-yl)-3-nitropyridin-2-amine (Intermediate 7, 0.8 g) and [(1S)-1-(5-fluoropyridin-2-yl)ethyl]amine hydrochloride (Intermediate 5, 0.4 g) in n-BuOH (10 mL) with diisopropylethylamine (2 mL) was stirred at 70° C. for 4 hours. The resulting mixture was diluted with ethyl acetate (20 mL), and washed with brine (10 mL×3). The organic layer was dried and concentrated. The resulting residue was separated by silica gel column (Hexane/Ethyl acetate) to yield 0.6 g of desired product. MS (electrospray): 402 (M+1) for C18H20FN7O3. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.3 (s, 1H) 11.0 (s, 1H) 8.80 (m, 1H) 8.50 (m, 1H) 8.15 (m, 1H) 7.80 (m, 1H) 7.30 (m, 1H) 6.20 (d, 1H) 5.80 (m, 1H) 5.35 (m, 1H), 4.60 (m, 1H) 1.50 (d, 3H) 1.20 (d, 6H).

後処理

  1. washwashed with brine (10 mL×3)
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe resulting residue was separated by silica gel column (Hexane/Ethyl acetate)

出典と根拠

ORDレコード
ord-46f1265773924246a2f01bbbec0fa671
出典データセット
uspto-grants-2013_07
特許番号
US08486966B2

反応ノート

読み込み中…