1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136041835, compound

HRID 880199Notes

Reaction equation

HRID 880199 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[C:15]=1[OH:21].[N:22]1([C:28]2[N:29]=[C:30]([CH2:35][C:36]([O-])=[O:37])[NH:31][C:32](=[O:34])[CH:33]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[Na+]>N1C=CC=CC=1>[Br:20][C:16]1[C:15]([OH:21])=[C:14]([NH:13][C:36](=[O:37])[CH2:35][C:30]2[NH:31][C:32](=[O:34])[CH:33]=[C:28]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:29]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 155315062-Amino-6-bromophenolHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136041835HCID 136041835, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

600 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 550 mg of 2-amino-6-bromophenol are added to a solution of 500 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 2 of example 1, in 4 ml of pyridine. The reaction mixture is stirred at ambient temperature for 20 hours, and then concentrated under reduced pressure. Water and ethyl acetate are added and the resulting mixture is thus stirred for 30 minutes. The precipitate formed is filtered off, and rinsed with water, ethyl ether and petroleum ether. The solid obtained is dried under vacuum. 543 mg of N-(3-bromo-2-hydroxyphenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the form of a beige solid, the characteristics of which are the following:

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater and ethyl acetate are added
  3. stirringthe resulting mixture is thus stirred for 30 minutes
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed with water, ethyl ether and petroleum ether
  7. customThe solid obtained
  8. customis dried under vacuum

Sources & evidence

ORD record
ord-07d9253c62334088b05f7954420af04e
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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