4-Cyano-2-methoxyphenylboronic acid → 1-(4-cyano-2-methoxyphenyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([N:15](CC3C=CC(OC)=CC=3OC)[C:16]3[S:20][N:19]=[CH:18][N:17]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([F:32])=[CH:4][N:3]=1.[C:33]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[C:37]([O:44][CH3:45])[CH:36]=1)#[N:34]>>[C:33]([C:35]1[CH:40]=[CH:39][C:38]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]4[S:20][N:19]=[CH:18][N:17]=4)(=[O:14])=[O:13])=[CH:9][CH:10]=3)[C:5]([F:32])=[CH:4][N:3]=2)=[C:37]([O:44][CH3:45])[CH:36]=1)#[N:34]Participants
Procedure
The title compound was prepared in an analogous manner to that of EXAMPLE 228, except that 1-chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide and (4-cyano-2-methoxyphenyl)boronic acid were used as the coupling partners. The final compound was purified via column chromatography (RediSep Gold 12 g silica gel column, gradient elution 0-10% MeOH:DCM) to afford 1-(4-cyano-2-methoxyphenyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ=8.76 (d, J=1.4 Hz, 1H), 8.50 (d, J=1.4 Hz, 1H), 8.48 (s, 1H), 8.00 (dd, J=1.7, 8.9 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 7.76 (s, 1H), 7.62 (dd, J=1.1, 7.7 Hz, 1H), 7.57-7.52 (m, 1H), 3.72 (s, 3H). m/z (ESI) 442.2 (M+H)+.
Workup
- customThe title compound was prepared in an analogous manner to that of EXAMPLE 228
- customThe final compound was purified via column chromatography (RediSep Gold 12 g silica gel column, gradient elution 0-10% MeOH:DCM)
Sources & evidence
- ORD record
- ord-8d9a31b26b6240c7a8c1a2380731fd81
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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