1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136041776, compound

HRID 1890478Notes

Reaction equation

HRID 1890478 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.[CH:20]1([NH:23][C:24]2[C:25]([NH2:31])=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH2:22][CH2:21]1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O.C(O)(=O)C>[CH:20]1([N:23]2[C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[N:31]=[C:15]2[CH2:14][C:9]2[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[N:8]=2)[CH2:22][CH2:21]1

Participants

7

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86762000HCID 86762000, compoundHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136041776HCID 136041776, compoundYield 3.5%

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, 645 mg of N1-cyclopropyl-4-fluorobenzene-1,2-diamine hydrochloride and 330 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 3 ml of pyridine and 3 ml of dimethylformamide and then in 5 ml of acetic acid. After refluxing for two hours and purification by silica column chromatography, eluent: CH2Cl2/MeOH: 95/05, the residue obtained is purified by preparative HPLC/MS (method 1). After the acetonitrile has been evaporated off, the pH is brought to 8 using sodium bicarbonate (solid), then the aqueous phase is extracted with twice 25 ml of ethyl acetate, and the combined organic phases are dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure. 15 mg of 2-[(1-cyclopropyl-5-fluoro-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 two hours
  3. custompurification by silica column chromatography, eluent
  4. customCH2Cl2/MeOH: 95/05, the residue obtained
  5. customis purified by preparative HPLC/MS (method 1)
  6. customAfter the acetonitrile has been evaporated off
  7. extractionthe aqueous phase is extracted with twice 25 ml of ethyl acetate
  8. dry with materialthe combined organic phases are dried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e63c257a821c499faf07c15162d2a494
Source dataset
uspto-grants-2013_08
Patent number
US08507483B2

Reaction notes

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