Cyclobutylamine → 1-cyclobutyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 2410116노트

반응식

HRID 2410116 반응식
[CH2:1]([O:3][C:4](=[O:12])/[C:5](/[N+:10]#[C-:11])=[CH:6]/[N:7]([CH3:9])C)[CH3:2].[CH:13]1(N)[CH2:16]C[CH2:14]1>>[CH2:1]([O:3][C:4]([C:5]1[N:10]=[CH:11][N:7]([CH:9]2[CH2:16][CH2:13][CH2:14]2)[CH:6]=1)=[O:12])[CH3:2]

참가 물질

3

반응물 2

HCID 75645CyclobutylamineHCID 10975874HCID 10975874, 화합물

생성물 1

HCID 866721321-cyclobutyl-1H-imidazole-4-carboxylic acid ethyl ester

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온도
70 °C

실험 절차

The stirred mixture of (Z)-3-dimethylamino-2-isocyano-acrylic acid ethyl ester (17.0 g, 100 mmol) and cyclobutaneamine (21.79 g, 300 mmol) was heated for 2.5 h at 70° C. The reaction mixture was cooled to rt and concentrated. The residue was purified by flash chromatography (EtOAc/hexane, 5:1) to afford the title compound as an orange oil. tR: 0.70 min (LC-MS 2); ESI-MS: 195.2 [M+H]+ (LC-MS 2); 1H-NMR (DMSO-d6, 400 MHz) δ ppm 8.03 (s, 1H), 7.83 (s, 1H), 4.73 (m, 1H), 4.18 (q, 2H), 2.36 (m, 4H), 1.74 (m, 2H), 1.24 (t, 3H).

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (EtOAc/hexane, 5:1)

출처 및 근거

ORD 기록
ord-b720a9a4128b4cf096242440c56978d8
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815926B2

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