5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide → 1-(2-Phenylpyrrolidin-1-YL)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide

HRID 1473464Notes

Reaction equation

HRID 1473464 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:17][CH:18]=[CH:19][N:20]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.ClC1C=C(C(F)(F)F)C=CC=1C1C=CC=C2C=1C=CC(S(NC1C=CN=CN=1)(=O)=O)=C2.C(C1C=C(C(F)(F)F)C=C[C:66]=1[C:75]1[C:84]2[C:79](=[CH:80][C:81](S(N(CC3C=CC(OC)=CC=3OC)C3SC=CN=3)(=O)=O)=[CH:82][CH:83]=2)[CH:78]=[CH:77][N:76]=1)#N>>[C:84]1([CH:75]2[CH2:66][CH2:78][CH2:77][N:76]2[C:2]2[C:11]3[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]4[S:17][CH:18]=[CH:19][N:20]=4)(=[O:13])=[O:14])=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1

Participants

4

Reactant 3

HCID 866873685-(2-chloro-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)naphthalene-2-sulfonamideHCID 866873781-chloro-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamideHCID 866874981-(2-cyano-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

Product 1

HCID 866875111-(2-Phenylpyrrolidin-1-YL)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide

Procedure

Example 237 was synthesized in a similar manner to Example 236, except that 1-chloro-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (Intermediate OOO) was used instead of 1-chloro-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (Intermediate X). Isolated 1-(2-cyano-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=12.87 (br. s., 1H), 8.51 (br. s., 1H), 8.29 (br. s., 1H), 7.84 (br. s., 1H), 7.78 (d, J=9.1 Hz, 1H), 7.36 (d, J=7.4 Hz, 3H), 7.32-7.22 (m, 2H), 7.18 (d, J=5.9 Hz, 1H), 6.87 (d, J=4.4 Hz, 1H), 5.59 (br. s., 1H), 4.36 (br. s., 1H), 3.92 (br. s., 1H), 2.02 (br. s., 2H), 1.90 (br. s., 2H). m/z (ESI) 437.2 (M+H)+.

Sources & evidence

ORD record
ord-6bfb0027e3d947428603e31abe982407
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

Loading…