2-[(S)-1-Phenylethylamino]-4-[5-azidobenzimidazol-1-yl]pyrimidine → 2-[(S)-1-Phenylethylamino]-4-[5-(4-ethoxycarbonyltriazol-1-yl)benzimidazol-1-yl]pyrimidine

HRID 2300815ノート

反応式

HRID 2300815 の反応式
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([N:25]=[N+:26]=[N-:27])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:28]([O:30][C:31](=[O:38])[CH:32]=[C:33](NC)NC)[CH3:29]>O1CCOCC1>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([N:25]5[CH:33]=[C:32]([C:31]([O:30][CH2:28][CH3:29])=[O:38])[N:27]=[N:26]5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 599246482-[(S)-1-Phenylethylamino]-4-[5-azidobenzimidazol-1-yl]pyrimidineHCID 85819813Ethyl 3,3-dimethylaminoacrylate

生成物 1

HCID 599247352-[(S)-1-Phenylethylamino]-4-[5-(4-ethoxycarbonyltriazol-1-yl)benzimidazol-1-yl]pyrimidine

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A solution containing 12.5 mg of 2-[(S)-1-phenylethylamino]-4-[5-azidobenzimidazol-1-yl]pyrimidine and about 100 μL ethyl-3,3-dimethylaminoacrylate in 2 mL 1,4-dioxane was stirred at 90° C. for 48 hours. The solution was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with methanol in methylene chloride to give 6.0 mg of the title compound. RF: 0.4 (5% MeOH in CH2Cl2). 1H NMR (500 MHz, 1:1 CD3OD/CDCl3): δ 1.42 (t, J=7.1 Hz, 3H), 1.59 (d, J=7.1 Hz, 3H), 4.44 (q, J=7.1 Hz, 2H), 5.16 (m, 1H), 6.92 (d, J=5.5 Hz, 1H), 7.24 (br s, J=7.3 Hz, 1H), 7.36 (br s, J=7.3 Hz, 2H), 7.45 (d, J=7.3 Hz, 2H), 7.68-7.8 (m, 1H), 7.95 (m, 1H), 8.14 (br s, 1H), 8.38 (br s, J=5.3 Hz, 1H), 8.77 (m, 1H), 8.92 (s, 1H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 455.2 (M+1).

後処理

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography
  3. washeluting with methanol in methylene chloride

出典と根拠

ORDレコード
ord-a70ccf3d2b9a4274b1ba8bd0f47fe23c
出典データセット
uspto-grants-2002_12
特許番号
US06498165B1

反応ノート

読み込み中…