1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 66882257, compound

HRID 880142Notes

Reaction equation

HRID 880142 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:4]=[C:3]1[CH2:15][C:16]([O-:18])=O.[Na+].[F:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1[O:28][CH3:29].Cl.CN(C)CCCN=C=NCC.C(Cl)Cl.CO>N1C=CC=CC=1.CN(C)C=O>[F:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:16](=[O:18])[CH2:15][C:3]2[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[C:5]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[N:4]=2)=[CH:23][C:22]=1[O:28][CH3:29]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27745334-Fluoro-3-methoxyanilineHCID 21226129Dichloromethane methanolHCID 57523684Sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

Product 1

HCID 66882257HCID 66882257, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The product is prepared according to the procedure described in example 5, using 200 mg of sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 1 of example 68, 205 mg of 4-fluoro-3-methoxyaniline, and 185 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 0.12 ml of pyridine and 3 ml of N,N-dimethylformamide. After extractions with ethyl acetate and silica column purification of the residue obtained, eluent: 95/05 then 90/10 CH2Cl2/MeOH, 42 mg of N-(4-fluoro-3-methoxyphenyl)-2-[1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. extractionAfter extractions
  3. customwith ethyl acetate and silica column purification of the residue
  4. customobtained

Sources & evidence

ORD record
ord-4b3bba1dcfc84f46910adb3eac6dee66
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

Loading…