tert-Butyl carbazate → tert-butyl N'-{2-[1-(2,6-dichlorobenzyl)-3-methyl-1H-indazole-6-yl]acetyl}hydrazinecarboxylate

HRID 2199989Notes

Reaction equation

HRID 2199989 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:15](O)=[O:16])[CH:12]=2)[C:7]([CH3:18])=[N:6]1.[C:24]([O:28][C:29](=[O:32])[NH:30][NH2:31])([CH3:27])([CH3:26])[CH3:25].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:15]([NH:31][NH:30][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:32])=[O:16])[CH:12]=2)[C:7]([CH3:18])=[N:6]1

Participants

6

Reactant 4

HCID 70091tert-Butyl carbazateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 60152151HCID 60152151, compound

Product 1

HCID 118237099tert-butyl N'-{2-[1-(2,6-dichlorobenzyl)-3-methyl-1H-indazole-6-yl]acetyl}hydrazinecarboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the compound [97] (73.2 mg) in chloroform (1.1 mL) were added tert-butylcarbazate (222.0 mg), 1-hydroxybenzotriazole monohydrate (113.5 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (161.0 mg) at room temperature, and then the reaction mixture was stirred for 18 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (84.0 mg) as a white solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-15d0549f986446e08783f9d5b79f9477
Source dataset
uspto-grants-2016_06
Patent number
US09359350B2

Reaction notes

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