1-Acetylpiperazine → 3-((4-acetylpiperazin-1-yl)methyl)-10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide
Reaction equation
[Br:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([CH:19]=O)=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:21]=1.[C:23]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)(=[O:25])[CH3:24]>>[C:23]([N:26]1[CH2:31][CH2:30][N:29]([CH2:19][C:13]2[N:8]3[CH:9]4[CH2:12][CH:11]([C:5]5[CH:4]=[C:3]([F:22])[C:2]([Br:1])=[CH:21][C:6]=5[C:7]3=[N:15][C:14]=2[C:16]([NH2:18])=[O:17])[CH2:10]4)[CH2:28][CH2:27]1)(=[O:25])[CH3:24]Participants
3
Procedure
10-bromo-9-fluoro-3-formyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide (75 mg) was reacted with N-acetylpiperazine similarly to as described in the synthesis of 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-3-[(4-methylpiperazin-1-yl)methyl]-5,6,7,12-tetrahydro-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide to afford 3-((4-acetylpiperazin-1-yl)methyl)-10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide which was directly reacted with 2-Methyl-3-butyne-ol via General Procedure E to afford 41 mg (41%) of 3-[(4-acetylpiperazin-1-yl)methyl]-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6,7,12-tetrahydro-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide. M+1=480.
Sources & evidence
- ORD record
- ord-c5847188eadf4001a9d7e3702af58a50
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034866B2
Reaction notes
Loading…