Dimethylformamide → 6-(2-Ethylaminopyrimidin-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (2amino-4-chlorophenyl)amide

HRID 12271

Reaction equation

HRID 12271 reaction equation
[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([C:10]2[CH:11]=[C:12]([C:17]([OH:19])=O)[C:13](=[O:16])[NH:14][N:15]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2].CN(C=O)C.C(N(CC)CC)C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([NH2:39])=[C:35]([NH2:40])[CH:34]=1>O>[NH2:40][C:35]1[CH:34]=[C:33]([Cl:32])[CH:38]=[CH:37][C:36]=1[NH:39][C:17]([C:12]1[C:13](=[O:16])[NH:14][N:15]=[C:10]([C:8]2[CH:7]=[CH:6][N:5]=[C:4]([NH:3][CH2:1][CH3:2])[N:9]=2)[CH:11]=1)=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72634-Chloro-1,2-diaminobenzeneHCID 8471TriethylamineHCID 684533256-(2-Ethylaminopyrimidin-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid

Product 1

HCID 866116046-(2-Ethylaminopyrimidin-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (2amino-4-chlorophenyl)amide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 110 mg of 6-(2-ethylaminopyrimidin-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid, 2 ml of DMF and 0.17 ml of triethylamine is mixed with 192 mg of Hatu and stirred at room temperature for 30 minutes. Then 66 mg of 4-chloro-phenylenediamine are added, and the mixture is stirred at room temperature overnight. 5 ml of water are added to the mixture, and the precipitate is briefly stirred and then filtered off with suction and dried.

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. stirringthe precipitate is briefly stirred
  3. filtrationfiltered off with suction
  4. customdried

Sources & evidence

ORD record
ord-c6db62493a0541ae9904ac2a0c41fb10
Source dataset
uspto-grants-2010_06
Patent number
US07727989B2

Linked notes

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