HCID 23125017, compound → HCID 23125005, compound

HRID 2223365Notes

Reaction equation

HRID 2223365 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:23]=[CH:22][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:13][C:12]=2[N+:24]([O-])=O)=[O:10])=[N:6][CH:7]=1>O1CCCC1.[Ni]>[NH2:24][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][C:11]=1[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:10])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

4

Reactant 1

HCID 23125017HCID 23125017, compound

Product 1

HCID 23125005HCID 23125005, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

t-Butyl 4-{[(5-chloropyridin-2-yl)amino]-carbonyl}-3-nitrobenzoate (3.2 g) obtained in Example 2(1) is dissolved in tetrahydrofuran (50 ml) and thereto is added Raney nickel, and the mixture is stirred at room temperature under hydrogen pressure (3 atm.) overnight. The insoluble materials are removed by filtration on Celite and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=20/1) to give t-butyl 3-amino-4-{[(5-chloropyridin-2-yl)amino]carbonyl}benzoate (2.3 g). APCI-MS M/Z: 348[M+H]+

Workup

  1. customThe insoluble materials are removed by filtration on Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-ff84efa0aa3b4308891ee84b171c5d8a
Source dataset
uspto-grants-2008_05
Patent number
US07375119B2

Reaction notes

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