Water → N-(3,4-dichlorobenzyl)-N'-1H-indazol-4-ylurea

HRID 887229Notes

Reaction equation

HRID 887229 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][N:14]2C(OC)=O)=[O:8].[OH-].[K+].C(Cl)Cl.O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 22032594Methyl 4-({[(3,4-dichlorobenzyl)amino]carbonyl}amino)-1H-indazole-1-carboxylate

Product 1

HCID 9997058N-(3,4-dichlorobenzyl)-N'-1H-indazol-4-ylurea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 90C (0.25 g, 0.6 mmol) was heated at reflux in methanol (5 mL) and 0.5N KOH (1 mL) for 0.5 hours. The reaction mixture was allowed to cool to ambient temperature, pH was adjusted to 5, and volume was reduced under reduced pressure. Methylene chloride and water was added, the phases were separated, and the organic phase concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 4.38 (d, 2H), 6.9 (t, 1H), 7.05 (d, 1H), 7.19 (t, 1H), 7.35 (dd, 1H), 7.6 (m, 2H), 8.06 (s, 1H), 8.82 (s, 1H). MS (DCI+) m/z 336 (M+H)+; Anal. Calcd. For C15H13N4Cl2O: C, 53.75; H, 3.62; N, 16.72. Found: C, 53.84; H, 3.44; N, 16.88.

Workup

  1. customthe phases were separated
  2. concentrationthe organic phase concentrated under reduced pressure

Sources & evidence

ORD record
ord-fde9c08b7dba4380a13cce8e1586ec97
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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