5-Aminoisoquinoline → N-[1-(4-chlorophenyl)-1-methylethyl]-N'-5-isoquinolinylurea

HRID 586058Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:11]=[C:12]=[O:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH:14]1[C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([NH2:24])[C:18]=2[CH:17]=[CH:16][N:15]=1.BrC1C=CC(CN=C=O)=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:11][C:12]([NH:24][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:18]=2[CH:17]=[CH:16][N:15]=[CH:14]3)=[O:13])([CH3:10])[CH3:9])=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 707665-Aminoisoquinoline

HCID 43746174-Bromobenzyl isocyanate

HCID 131183231-Chloro-4-(2-isocyanatopropan-2-yl)benzene

Product 1

HCID 10404960N-[1-(4-chlorophenyl)-1-methylethyl]-N'-5-isoquinolinylurea

Procedure

The title compound was prepared using the procedure described in Example 60F using 1-chloro-4-(1-isocyanato-1-methylethyl)benzene and 5-isoquinolinamine instead of the product from Example 60E and 1-bromo-4-(isocyanatomethyl)benzene. MS (ESI+) m/z 355 (M+H)+; MS (ESI−) m/z 353 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.63 (s, 6H), 7.23 (s, 1H), 7.37 (d, J 8.8, 2H), 7.47 (d, J 8.8, 2H), 7.73 (t, J 9.2, 1H), 7.93 (d, J 8.1, 1H), 8.25 (d, J 6.4, 1H), 8.39 (d, J 8.1, 1H), 8.67 (d, J 6.4, 1H), 8.87 (s, 1H), 9.58 (s, 1H); Anal. Calcd for C19H18ClN3O.HCl+0.25EtOH: C, 60.40; H, 5.33; N, 10.54. Found: C, 60.82; H, 5.23; N, 10.45.

Sources & evidence

ORD record: ord-6a14ffd854604eff8b8f24b900cb8dfc
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933311B2

Reaction notes

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