4-Chloro-1,2-diaminobenzene → HCID 136041775, compound

HRID 1890477Notes

Reaction equation

HRID 1890477 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+].[Cl:19][C:20]1[CH:21]=[C:22]([NH2:27])[C:23]([NH2:26])=[CH:24][CH:25]=1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O.C(O)(=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]2[N:26]=[C:15]([CH2:14][C:9]3[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[N:8]=3)[NH:27][C:22]=2[CH:21]=1

Participants

7

Reactant 3

HCID 72634-Chloro-1,2-diaminobenzeneHCID 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 136041775HCID 136041775, compoundYield 49.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The product is prepared according to the procedure described in Example 3, using 400 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, 436 mg of 4-chlorobenzene-1,2-diamine and 440 mg N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 3.5 ml of pyridine and 3.5 ml of dimethylformamide and then in 7 ml of acetic acid. After refluxing for thirty minutes and purification by silica column chromatography, eluent: CH2Cl2/MeOH: gradient from 100/0 to 90/10, 260 mg of 2-[(6-chloro-1H-benzimidazol-2-yl)methyl]-6-(morpholin-4-yl)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. temperatureAfter refluxing for thirty minutes
  3. custompurification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-8dabe09c34084996964587c7bd1d7dea
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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