2-Benzimidazolyl-1-(2,4-dichlorophenyl)-3(dimethylamino)prop-2-en-1-one → [5-Benzimidazolyl-4-(2,4-dichlorophenyl)pyrimidin-2-yl]{2-[(5-nitro(2-pyridyl))amino]ethyl}amine dihydrochloride

HRID 31930Notes

Reaction equation

HRID 31930 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[C:16]([C:17]2C=CN[N:18]=2)=[CH:15][N:14]=[C:13]([NH:22][CH2:23][CH2:24][NH:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][N:27]=2)[N:12]=1.[N:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2NC=1C(=CN(C)C)C(C1C=CC([Cl:53])=CC=1Cl)=O>>[ClH:3].[ClH:53].[N:18]1[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[NH:35][C:17]=1[C:16]1[C:11]([C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=2[Cl:3])=[N:12][C:13]([NH:22][CH2:23][CH2:24][NH:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][N:27]=2)=[N:14][CH:15]=1

Participants

3

Reactant 2

HCID 538346012-Benzimidazolyl-1-(2,4-dichlorophenyl)-3(dimethylamino)prop-2-en-1-oneHCID 178478900HCID 178478900, compound

Product 1

HCID 69308291[5-Benzimidazolyl-4-(2,4-dichlorophenyl)pyrimidin-2-yl]{2-[(5-nitro(2-pyridyl))amino]ethyl}amine dihydrochloride

Procedure

Made using the same procedure as for [4-(2,4-dichlorophenyl)-5-pyrazolylpyrimidin-2-yl]{2-[(5-nitro(2-pyridyl))amino]ethyl}amine dihydrochloride except that 2-benzimidazolyl-1-(2,4-dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one (XIV, 468 mg, 1.3 mmol) was used and the crude product was purified by recrystallization (CH2Cl2/Et2O/hexanes).

Workup

  1. customthe crude product was purified by recrystallization (CH2Cl2/Et2O/hexanes)

Sources & evidence

ORD record
ord-5ef4a6ec51e24330b9fddb1b892d9c5b
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Reaction notes

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