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

HRID 1791312Notes

Reaction equation

HRID 1791312 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 C19H18CIN3O HCl 0.25 EtOH: C, 60.40; H, 5.33; N, 10.54. Found: C, 60.82; H, 5.23; N, 1045.

Workup

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

Sources & evidence

ORD record
ord-b1299c6fa1584a449bf4be13c0a1832e
Source dataset
uspto-grants-2006_07
Patent number
US07074805B2

Reaction notes

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