2-Fluoro-4-(oxiran-2-yl)benzonitrile → 2-Fluoro-4-(1-hydroxy-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile
Reaction equation
[OH:1][CH:2]([C:10]1[CH:19]=[CH:18][C:13]2[C:14](=[O:17])[O:15][CH2:16][C:12]=2[C:11]=1[CH3:20])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[F:21][C:22]1[CH:29]=[C:28]([CH:30]2[CH2:32][O:31]2)[CH:27]=[CH:26][C:23]=1[C:24]#[N:25]>>[F:21][C:22]1[CH:29]=[C:28]([CH:30]([OH:31])[CH2:32][N:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([OH:1])[C:10]3[CH:19]=[CH:18][C:13]4[C:14](=[O:17])[O:15][CH2:16][C:12]=4[C:11]=3[CH3:20])[CH2:5][CH2:6]2)[CH:27]=[CH:26][C:23]=1[C:24]#[N:25]Participants
3
Procedure
2-fluoro-4-(1-hydroxy-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile was prepared in a similar fashion to that described for the synthesis of EXAMPLES 2C and 28-29 starting from 5-(1-hydroxy-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one and 2-fluoro-4-oxiran-2-ylbenzonitrile. 1H NMR (500 MHz, DMSO-d6), δ 7.98 (m, 1H), 7.74 (m, 1H), 7.71 (m, 1H), 7.60 (d, J=10.5 Hz, 1H), 7.52 (d, J=7.9 Hz, 1H), 5.56 (d, J=7.7 Hz, 1H), 5.42 (dd, J=8.3 Hz, 2H), 5.38 (bs, 1H), 3.95-3.42 (m, 6H), 3.40-3.18 (m, 6H), 2.36 (s, 3H); LC/MS (M+1)+=440.02.
Sources & evidence
- ORD record
- ord-5512dd503f214c3385f5eecc1e1395ea
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673920B2
Reaction notes
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