Methylamine → 2-Acetamido-8-chloro-6-methylbenzo[c][2,7]naphthyridin-6-ium fluoride
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=O)=[CH:12][N:11]=[C:10]([NH:16][C:17](=[O:19])[CH3:18])[CH:9]=2)=[C:4]([F:20])[CH:3]=1.[CH3:21][NH2:22]>ClCCl>[F-:20].[C:17]([NH:16][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][N:11]=1)[CH:14]=[N+:22]([CH3:21])[C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]2=1)(=[O:19])[CH3:18]Participants
4
Procedure
To a stirred solution of N-(4-(4-chloro-2-fluorophenyl)-5-formylpyridin-2-yl)acetamide (0.39 g, 1.332 mmol) and 4 Å molecular sieves (50 mg) in dichloromethane (35 mL) at 0° C. was added methyl amine (8M in EtOH, 0.041 g, 0.166 mL, 1.332 mmol) dropwise and the reaction was stirred at rt overnight (12 h). The reaction mixture was diluted with DCM (40 mL) and filtered through a bed of diatomaceous earth (Celite®). The filtrate was concentrated under reduced pressure to afford 2-acetamido-8-chloro-6-methylbenzo[c][2,7]naphthyridin-6-ium fluoride (450 mg, 1.24 mmol, 93% yield) as a yellow solid that was used in the next step without purification. LC/MS (ESI) m/e 286.1 [(M)+, calcd for C15H13ClN3O 286.1]; LC/MS retention time (Method D): tR=0.71 min.