Pyrrolidine → 5-(4-bromophenyl)-5-(2-oxo-2-pyrrolidin-1-ylethyl)-5H-imidazo[2,1-a]isoindole

HRID 46168노트

반응식

HRID 46168 반응식
[CH:1]1[CH:6]=[N:5][C:4]2N(O)N=N[C:3]=2C=1.FC(F)(F)C([O-])=O.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2([CH2:37][C:38]([OH:40])=O)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]3=[NH+:34][CH:35]=[CH:36][N:26]23)=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C.N1CCCC1>CN(C=O)C.C(Cl)CCl>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2([CH2:37][C:38](=[O:40])[N:5]3[CH2:4][CH2:3][CH2:1][CH2:6]3)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]3=[N:34][CH:35]=[CH:36][N:26]23)=[CH:23][CH:24]=1

참가 물질

7

반응물 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 1785249895-(4-bromophenyl)-5-(carboxymethyl)-5H-imidazo[2,1-a]isoindol-1-ium trifluoroacetate

생성물 1

HCID 462023775-(4-bromophenyl)-5-(2-oxo-2-pyrrolidin-1-ylethyl)-5H-imidazo[2,1-a]isoindole

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of EDC (49.2 mg) and HOAT (17.5 mg) was added a solution of 5-(4-bromophenyl)-5-(carboxymethyl)-5H-imidazo[2,1-a]isoindol-1-ium trifluoroacetate (62 mg) and Hunig's base (0.134 mL) in DMF (1 mL) followed by pyrrolidine (22.8 mg). The reaction mixture was stirred overnight at room temperature and was then purified by reversed phase HPLC (21×100 mm Phenomenex Gemini, 15-70% MeCN/water containing 0.05% NH4OH over 20 min at 20 mL/min) to give title compound as a white solid. HRMS. Found, 422.0873; calcd for (M+H)+, 422.0863. 1H NMR (500 MHz, CDCl3): δ 7.84 (d, J=7.60 Hz, 1 H); 7.47 (d, J=1.30 Hz, 1 H); 7.42-7.39 (m, 3 H); 7.29-7.26 (m, 3 H); 6.91 (dd, J=21.03, 8.48 Hz, 2 H); 3.71 (d, J=16.82 Hz, 1 H); 3.42 (t, J=6.89 Hz, 2 H); 3.34 (dt, J=9.85, 6.85 Hz, 1 H); 3.18 (dt, J=9.89, 6.80 Hz, 1 H); 2.86 (d, J=16.81 Hz, 1 H); 1.95-1.79 (m, 4 H).

후처리

  1. customwas then purified by reversed phase HPLC (21×100 mm Phenomenex Gemini, 15-70% MeCN/water containing 0.05% NH4OH over 20 min at 20 mL/min)

출처 및 근거

ORD 기록
ord-6d64d62dbb1341fd91bfb24ba02aa77c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541595B2

반응 노트

불러오는 중…