Diisopropylethylamine → HCID 178423604、化合物

HRID 243279ノート

反応式

HRID 243279 の反応式
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([C@@H:11]([NH2:13])[CH3:12])[N:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl[C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][NH:25]2.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([C@@H:11]([NH:13][C:21]3[N:29]=[CH:28][N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][NH:25]4)[CH3:12])[N:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 68157022(S)-1-(4-Methyl-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamineHCID 178478393HCID 178478393、化合物

生成物 1

HCID 178423604HCID 178423604、化合物

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of (S)-1-(4-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine from Example 3 (100 mg, 0.398 mmol), 6-chloro-9H-purine (68 mg, 0.438 mmol) and DIPEA (83 μL, 0.478 mmol) in n-butanol (1 mL) was stirred in a sealed vial at 100° C. for 20 h. After cooling to RT, the mixture was partitioned between DCM and water. The organic layer was then separated, dried and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) and then sonicated in cyclohexane affording 108 as an off-white solid (56 mg, 38%) LCMS: RT 3.17 min [M+H]+ 370.1. 1H NMR (DMSO, 400 MHz): δ 8.13 (1H, bs), 8.08 (1H, s), 7.96-7.85 (1H, m), 7.67-7.44 (5H, m), 7.12-6.99 (2H, m), 6.86 (1H, d, J=7.80 Hz), 5.49 (1H, br), 2.56 (3H, s), 1.57 (3H, d, J=6.86 Hz)

後処理

  1. temperatureAfter cooling to RT
  2. customthe mixture was partitioned between DCM and water
  3. customThe organic layer was then separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)
  7. customsonicated in cyclohexane affording 108 as an off-white solid (56 mg, 38%) LCMS: RT 3.17 min [M+H]+ 370.1

出典と根拠

ORDレコード
ord-37375efb4e864dff9a715a06b3d684f4
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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