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Diisopropylcarbodiimide → 4-chloro-2-(4-nitrophenylamino)-3H-imidazo-[4,5-c]pyridine

HRID 641788
Notes
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Reaction equation

HRID 641788 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=S)=[CH:15][CH:14]=1)([O-:12])=[O:11].CC(N=C=NC(C)C)C>CN(C=O)C>[Cl:9][C:3]1[C:2]2[NH:1][C:20]([NH:19][C:16]3[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:18][CH:17]=3)=[N:8][C:7]=2[CH:6]=[CH:5][N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 75044Benzene, 1-isothiocyanato-4-nitro-HCID 2857362-Chloropyridine-3,4-diamine

Product 1

HCID 1785266824-chloro-2-(4-nitrophenylamino)-3H-imidazo-[4,5-c]pyridineYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.1 A solution of 0.72 g of 3,4-diamino-2-chloropyridine, 0.9 g of 4-nitrophenyl isothiocyanate and 0.78 ml of N,N-diisopropylcarbodiimide in 30 ml of DMF is stirred at room temperature for 16 hours, then at 500 for 6 hours. The solvent is separated off, and the residue is crystallised from methanol, giving 1.2 g of 4-chloro-2-(4-nitrophenylamino)-3H-imidazo-[4,5-c]pyridine (“6”).

Workup

  1. customThe solvent is separated off
  2. customthe residue is crystallised from methanol

Sources & evidence

ORD record
ord-5af5aee4d7de41bbb82aa03f3bc06196
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696224B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes