2-(Pyridin-2-yl)but-3-yn-2-ol → (+/-)-9-fluoro-10-(3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide
Reaction equation
Br[C:2]1[C:3]([F:20])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[CH:13]=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:19]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([OH:31])([C:29]#[CH:30])[CH3:28]>>[F:20][C:3]1[C:2]([C:30]#[C:29][C:27]([OH:31])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)[CH3:28])=[CH:19][C:6]2[C:7]3[N:8]([CH:13]=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=3)[CH:9]3[CH2:12][CH:11]([C:5]=2[CH:4]=1)[CH2:10]3Participants
3
Reactant 2
Product 1
Procedure
9-fluoro-10-(3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was prepared similarly according to General Procedure G with slight modifications. 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was reacted with 2-(2-pyridyl)but-3-yn-2-ol to afford 7.5 mg of the titled compound (6.3% yield). M+1=403.1. 1H NMR (400 MHz, DMSO) δ 8.64 (d, J=7.6 Hz, 1H), 8.58 (d, J=4.6 Hz, 1H), 7.90-7.84 (m, 1H), 7.82 (s, 1H), 737 (d, J=7.9 Hz, 1H), 7.57 (br s, 1H), 7.38-7.32 (m, 1H), 7.29 (d, J=10.1 Hz, 1H), 7.11 (br s, 1H), 6.47 (s, 1H), 4.94-4.87 (m, 1H), 3.75-3.67 (m, 1H), 3.14-3.03 (m, 2H), 1.83 (s, 3H), 1.71-1.64 (m, 2H).
Workup
- custom9-fluoro-10-(3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was prepared similarly
Sources & evidence
- ORD record
- ord-8dba220497734016ad12b1049ed40645
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034866B2
Reaction notes
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