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 2300815노트

반응식

HRID 2300815 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-a70ccf3d2b9a4274b1ba8bd0f47fe23c
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498165B1

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