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

HRID 46168ノート

反応式

HRID 46168 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6d64d62dbb1341fd91bfb24ba02aa77c
出典データセット
uspto-grants-2013_09
特許番号
US08541595B2

反応ノート

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