Iodoethane → 2-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-ethyl-1H-benzo[d]imidazole

HRID 2202828노트

반응식

HRID 2202828 반응식
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH2:18][CH:17]([C:19]4[NH:23][C:22]5[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=5[N:20]=4)[CH2:16]3)[CH:9]=2)[N:3]=1.[CH2:28](I)[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH2:18][CH:17]([C:19]4[N:23]([CH2:28][CH3:29])[C:22]5[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=5[N:20]=4)[CH2:16]3)[CH:9]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 715503742-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole

생성물 1

HCID 715505172-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-ethyl-1H-benzo[d]imidazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

Example 107 (13 mg, 0.036 mmol), ethyl iodide (5.6 mg, 0.036 mmol), and cesium carbonate (58 mg, 0.18 mmol) were combined in degassed DMF (1 mL) and heated at 60° C. for 30 min. The mixture was cooled to room temperature, filtered and purified by reverse phase HPLC, providing Example 114 as a solid. 1H NMR: (400 MHz, d6-DMSO) δ 7.71-7.67 (m, 2H), 7.37-7.30 (m, 2H) 6.56 (s, 1H), 4.62-4.58 (m, 3H), 4.47-4.44 (m, 2H), 4.30 (q, J=7.2 Hz, 2H), 2.77 (s, 3H), 2.45 (s, 3H), 2.29 (s, 3H), 1.34 (t, J=7.1 Hz, 3H) ppm; MS: m/z=389.4 (M+H).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-267a359c969240b783ddd6389fcacc5a
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365562B2

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