1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-[1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]-N-phenylacetamide

HRID 880143Notes

Reaction equation

HRID 880143 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15]([O-:17])=O)[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na+].O1[C:23]2=[CH:24][CH:25]=[CH:26][C:27]([NH2:28])=[C:22]2C=C1.Cl.[CH3:30]N(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O>[CH3:30][N:10]1[C:11](=[O:13])[CH:12]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[N:8]=[C:9]1[CH2:14][C:15]([NH:28][C:27]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11423621Benzofuran-4-amineHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 498541212-[1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]-N-phenylacetamideYield 87.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The product is prepared according to the procedure described in example 5, using 250 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, 178 mg of 1-benzofuran-4-amine, and 300 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 2 ml of pyridine and 3 ml of N,N-dimethylformamide. 275 mg of 2-[1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]-N-phenylacetamide are obtained in the form of an off-white solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared

Sources & evidence

ORD record
ord-b0cfc2ee1b134435b2c38b17efeb362c
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

Loading…