HCID 57962341, compound → HCID 57962617, compound

HRID 541876Notes

Reaction equation

HRID 541876 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=3)[CH:10]=2)[C:5]([Cl:26])=[CH:4][N:3]=1>CO.[Pd]>[NH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][NH:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6]2[C:5]([Cl:26])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:10]=1

Participants

4

Reactant 1

HCID 57962341HCID 57962341, compound

Product 1

HCID 57962617HCID 57962617, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2,5-dichloropyrimidin-4-yl)-N′-(3-nitrobenzyl)benzene-1,3-diamine (2.00 g, 5.12 mmol) in methanol (30 mL) was added 10% palladium on carbon (200 mg, 0.2 mmol). The resultant mixture was hydrogenated at 25 psi for 18 h. The reaction mixture was filtered, washed with MeOH and concentrated to give the desired product (1.72 g, 93%) as a light yellow powder. LCMS for C17H16Cl2N5 (M+H)+: m/z=360.2.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c015a1e69d5b4a798da1d7e69cdd5924
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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