N-Phenyl-o-phenylenediamine → HCID 136041765, compound

HRID 1890471Notes

Reaction equation

HRID 1890471 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15]([O-])=O)[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na+].[C:19]1([NH:25][C:26]2[C:27]([NH2:32])=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O.C(O)(=O)C>[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15]3[N:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[N:32]=3)[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 68297N-Phenyl-o-phenylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136041765HCID 136041765, compoundYield 51.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The product is prepared according to the procedure described in Example 3, using 300 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, 423 mg of N-phenylbenzene-1,2-diamine and 330 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 2.5 ml of pyridine and 2.5 ml of dimethylformamide and then in 5 ml of acetic acid. After purification by silica column chromatography, eluent: CH2Cl2/MeOH: 95/05, 230 mg of 6-(morpholin-4-yl)-2-[(1-phenyl-1H-benzimidazol-2-yl)methyl]pyrimidin-4(3H)-one are obtained in the form of a white powder, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter purification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-71fb9cfb57fc4032a9b4255ab950f1ae
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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