HCID 86732071, compound → HCID 71548049, compound
Reaction equation
[NH:1]([C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([C@@H:10]2[CH2:12][C@H:11]2[C:13]2[N:17]([CH3:18])[C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[N:14]=2)[CH:4]=1)[NH2:2].CN(C)[C:25](=[N:27][C:28](=O)[CH2:29][O:30][CH3:31])[CH3:26]>C(O)(=O)C>[CH3:31][O:30][CH2:29][C:28]1[N:1]([C:3]2[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([C@@H:10]3[CH2:12][C@H:11]3[C:13]3[N:17]([CH3:18])[C:16]4[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=4[N:14]=3)[CH:4]=2)[N:2]=[C:25]([CH3:26])[N:27]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-((1R,2R)-2-(6-hydrazinyl-2-methylpyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (4-7, 25.0 mg, 0.0850 mmol, 1.0 eq) in acetic acid (3 mL) was added to a round bottom flask containing N-(1-(dimethylamino)ethylidene)-2-methoxyacetamide (200 mg, 1.26 mmol, 14.9 eq; prepared according to procedure 2-1). The acetic acid solution was heated at 100° C. for 30 minutes, allowed to cool to room temperature and concentrated to dryness. The residue was partitioned between saturated aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to dryness. The resulting residue was purified by reverse phase liquid chromatography (H2OCH3CN gradient w/ 0.1% NH4OH present) to afford 2-((1R,2R)-2-(6-(5-(methoxymethyl)-3-methyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (4-8) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.69 (m, 2H), 7.24 (m, 3H), 5.11 (s, 2H), 3.81 (s, 3H), 3.57 (s, 3H), 2.83 (m, 2H), 2.69 (s, 3H), 2.56 (s, 3H), 2.04 (m, 1H), 1.98 (m, 1H). HRMS m/z (M+H) 390.2039 found, 390.2037 required.