Hexane → Methyl 4-({[(3,4-dichlorobenzyl)amino]carbonyl}amino)-1H-indazole-1-carboxylate

HRID 585959

Reaction equation

HRID 585959 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:11]([O:13][CH3:14])=[O:12].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]=[C:24]=[O:25])=[CH:18][C:17]=1[Cl:26].CCCCCC>C1COCC1>[Cl:26][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][C:16]=1[Cl:15])[CH2:22][NH:23][C:24]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:11]([O:13][CH3:14])=[O:12])=[O:25]

Participants

5

Reactant 3

HCID 8058HexaneHCID 27333681,2-Dichloro-4-(isocyanatomethyl)benzeneHCID 22032652methyl 4-amino-1H-indazole-1-carboxylate

Product 1

HCID 22032594Methyl 4-({[(3,4-dichlorobenzyl)amino]carbonyl}amino)-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 90B (0.19 g, 1 mmol) in THF (3 mL) was treated with 1,2-dichloro-4-(isocyanatomethyl)benzene (0.22 g, 1.1 mmol) at ambient temperature. After stirring for 3 hours, hexane was added to the reaction mixture to precipitate the title compound as a tan solid (0.25 g). 1H NMR (300 MHz, DMSO-d6) δ 4.38 (d, 2H), 6.97 (t, 1H), 7.36 (dd, 1H), 7.48 (t, 1H), 7.6 (m, 2H), 7.7 (d, 1H), 7.8 (d, 1H), 8.45 (s, 1H), 9.16 (s, 1H).

Workup

  1. customto precipitate the title compound as a tan solid (0.25 g)

Sources & evidence

ORD record
ord-d9512e710f0a479b8c745e98b215f31b
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Linked notes

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