반응식
[N:1]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([OH:17])=O)=[CH:14][C:9]=2[N:8]=[CH:7]1)=[N+:2]=[N-:3].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH:37]12[NH:44][CH:41]([CH2:42][CH2:43]1)[CH2:40][CH:39]([OH:45])[CH2:38]2.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[N:1]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([N:44]3[CH:37]4[CH2:43][CH2:42][CH:41]3[CH2:40][CH:39]([OH:45])[CH2:38]4)=[O:17])=[CH:14][C:9]=2[N:8]=[CH:7]1)=[N+:2]=[N-:3]참가 물질
반응물 5
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 0 °C
실험 절차
To a solution of 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid (0.82 g, 0.00357 mol) in dry DMF (8.0 mL) was added with stirring HOBt (0.578 g, 0.00428 mol), DIPEA (1.9 mL, 0.0107 mol), 8-azabicyclo[3.2.1]octan-3-ol (0.5 g, 0.00393 mol) and the mixture was cooled to 0° C. To the resulting mixture was added EDCl (0.82 g, 0.00428 mol) and stirred for 15 h at ambient temperature. The reaction mixture was then diluted with ice water (100 mL), extracted with EtOAc (3×50 mL) and the combined organic phases were washed with water (3×50 mL) and saturated brine solution (50 mL). The organic phase was dried (Na2SO4) and the solvent evaporated affording (1.1 g, 98%) of [1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)methanone. MS-ESI m/z 341 (M+1).
후처리
- extractionextracted with EtOAc (3×50 mL)
- washthe combined organic phases were washed with water (3×50 mL) and saturated brine solution (50 mL)
- dry with materialThe organic phase was dried (Na2SO4)
- customthe solvent evaporated
출처 및 근거
- ORD 기록
- ord-5e615b6ab9244c5f843b5aa422e26add
- 출처 데이터셋
- uspto-grants-2011_11
- 특허 번호
- US08053431B2
연결된 노트
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