N-[(3-Chloro-pyrazin-2-yl)-(2-phenyl-quinolin-7-yl)-methyl]-acetamide → 7-(8-Chloro-3-methyl-imidazo[1,5-a]pyrazin-1-yl)-2-phenyl-quinoline

HRID 244092ノート

反応式

HRID 244092 の反応式
[Cl:1][C:2]1[C:3]([CH:8]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:20]3)=[CH:15][CH:14]=2)[NH:9][C:10](=O)[CH3:11])=[N:4][CH:5]=[CH:6][N:7]=1>O=P(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([CH3:11])=[N:9][C:8]=2[C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:20]3)=[CH:15][CH:14]=2)[CH:5]=[CH:6][N:7]=1

参加物

3

反応物 1

HCID 53629019N-[(3-Chloro-pyrazin-2-yl)-(2-phenyl-quinolin-7-yl)-methyl]-acetamide

生成物 1

HCID 536290187-(8-Chloro-3-methyl-imidazo[1,5-a]pyrazin-1-yl)-2-phenyl-quinoline

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
80 °C

実験手順

N-[(3-Chloro-pyrazin-2-yl)-(2-phenyl-quinolin-7-yl)-methyl]-acetamide (273.0 mg, 0.702 mmol) was dissolved in 20 mL of POCl3. The reaction was heated to 80° C. for 24 h. The excess POCl3 was removed in vacuo. The residue was worked up by basifying with cold 2.0 M NH3 in IPA followed by the addition of CH2Cl2 and water. The aqueous layer was washed with CH2Cl2 (2×). The organic layers where combined, dried over sodium sulfate, filtered and concentrated in vacuo to yield a light brown oil; 1H NMR (400 MHz, CDCl3) δ 2.77 (s, 3H), 7.41-7.59 (m, 4H), 7.70-7.72 (m, 1H), 7.88-7.93 (m, 3H), 8.19-8.28 (brm, 3H), 8.55 (brs, 1H); MS (ES+): 370.96 (M+1), 372.97 (M+3), 373.98 (M+4).

後処理

  1. customThe excess POCl3 was removed in vacuo
  2. additionfollowed by the addition of CH2Cl2 and water
  3. washThe aqueous layer was washed with CH2Cl2 (2×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a light brown oil

出典と根拠

ORDレコード
ord-33870cddf7e44a1280ce121298d06a3b
出典データセット
uspto-grants-2014_02
特許番号
US08653268B2

反応ノート

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