O-Phenylenediamine → HCID 136254283, compound

HRID 1890473Notes

Reaction equation

HRID 1890473 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([NH2:26])[C:20]([NH2:25])=[CH:21][CH:22]=[CH:23][CH:24]=1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O.C(O)(=O)C>[NH:25]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:26]=[C:15]1[CH2:14][C:9]1[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[N:8]=1

Participants

7

Reactant 3

HCID 7243O-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 136254283HCID 136254283, compoundYield 21%

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, 248 mg of benzene-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 refluxing for one hour and purification by silica column chromatography, eluent: CH2Cl2/MeOH: gradient from 100/0 to 90/10, 75 mg of 2-(1H-benzimidazol-2-ylmethyl)-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a beige powder, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. temperatureAfter refluxing for one hour
  3. custompurification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-9ee4c68caff942bab58216cb2e617891
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

Loading…