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

HRID 585942Notes

Reaction equation

HRID 585942 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:22]=[C:23]=[O:24])([CH3:21])[CH3:20])=[CH:15][CH:14]=1>C1COCC1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([NH:22][C:23]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]=[CH:7]3)=[O:24])([CH3:21])[CH3:20])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 707665-AminoisoquinolineHCID 131183231-Chloro-4-(2-isocyanatopropan-2-yl)benzene

Product 1

HCID 10404960N-[1-(4-chlorophenyl)-1-methylethyl]-N'-5-isoquinolinylureaYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared using 5-aminoisoquinoline, the product of Example 76B and the procedure described in Example 73B except that THF was used as solvent. The product was recrystallized from ethyl acetate to provide the title compound as a white solid (840 mg, 34%). MS (ESI+) m/z 355 (M+H)+; MS (ESI−) m/z 353 (M−H)−; 1H NMR (DMSO-d6, 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.

Workup

  1. customThe title compound was prepared
  2. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-df95c4d2a4804e878b8ed7195afaf9ea
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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