Toluene → Methyl 5-({[(4-bromobenzyl)amino]carbonyl}amino)isoquinoline-3-carboxylate

HRID 585935Notes

Reaction equation

HRID 585935 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[N:6]=[CH:7]2.C1(C)C=CC=CC=1.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]=[C:32]=[O:33])=[CH:26][CH:25]=1>C1COCC1>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][NH:31][C:32]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[N:6]=[CH:7]3)=[O:33])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 43746174-Bromobenzyl isocyanateHCID 22032628Methyl 5-aminoisoquinoline-3-carboxylate

Product 1

HCID 10409520Methyl 5-({[(4-bromobenzyl)amino]carbonyl}amino)isoquinoline-3-carboxylateYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product of Example 71B (0.156 g, 0.77 mmol) in THF:toluene (10 mL, 1:1) was treated with a solution of 1-bromo-4-(isocyanatomethyl)benzene (0.201 g, 0.95 mmol) in THF (1.0 mL). After stirring for 16 hours at room temperature, the reaction mixture was concentrated under reduced pressure and the residue was triturated with diethyl ether to provide the title compound as a tan solid (0.272 g, 85%). MS (ESI+) m/z 415 (M+H)+; MS (ESI−) m/z 413 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 3.95 (s, 3H), 4.36 (d, J 5.6, 2H), 7.23 (t, J 5.6, 1H), 7.33 (m, 2H), 7.56 (m, 2H), 7.76 (t, J 7.8, 1H), 7.85 (d, J 8.3, 1H), 8.41 (dd, J 1.5, 7.8, 11H), 8.82 (s, 1H), 9.06 (s, 1H), 9.35 (s, 1H); Anal. Calcd for C19H16BrN3O3: C, 55.09; H, 3.89; N, 10.14. Found: C, 55.06; H, 3.56; N, 9.84.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-bbe29aaf855d482da2dd15da8ae36877
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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