Ethylenediamine → HCID 71288354, compound

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=4)[N:23]([CH3:31])[N:22]=3)[N:19]=2)[N:14](COCC[Si](C)(C)C)[CH:13]=1)=[O:11])[CH3:8].C(Cl)Cl.C(N)CN>C(O)(C(F)(F)F)=O>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=4)[N:23]([CH3:31])[N:22]=3)[N:19]=2)[NH:14][CH:13]=1)=[O:11])[CH3:8]

Participants

Procedure

2-(6-Chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(1-methyl-1H-imidazol-2-yl)-ethyl]-amide (300 mg, 0.531 mol) was dissolved in a 4:6 solution of TFA:DCM (142 mL). After stirring at room temperature overnight, the volatiles were removed under reduced pressure. The crude material was then dissolved in dichloromethane and treated with ethylenediamine (319 mg, 5.31 mmol). After stirring at room temperature overnight, the precipitate was collected by filtration to afford 100 mg (43%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(1-methyl-1H-imidazol-2-yl)-ethyl]-amide as a yellow solid. MS: (M+H)+=435; 1H NMR (300 MHz, DMSO-d6) δ ppm 9.12 (s, 1H) 8.50-8.63 (m, 2H) 8.49-8.50 (m, 1H) 7.96 (d, J=1.51 Hz, 1H) 7.29 (dd, J=8.69, 1.51 Hz, 1H) 7.09 (s, 1H) 6.85 (s, 1H) 5.40-5.68 (m, 1H) 4.15 (s, 3H) 3.63-3.77 (m, 3H) 1.61 (d, J=6.80 Hz, 3H).