4-Fluoroaniline → HCID 136098467, compound

HRID 2278526Notes

Reaction equation

HRID 2278526 reaction equation
Cl.CN(C)CCCN=C=NCC.[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[Na].[CH3:22][CH:23]1[O:28][CH2:27][CH2:26][N:25]([C:29]2[N:30]=[C:31]([CH2:36][C:37](O)=[O:38])[NH:32][C:33](=[O:35])[CH:34]=2)[CH2:24]1>CN(C)C=O.N1C=CC=CC=1>[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:37](=[O:38])[CH2:36][C:31]2[NH:32][C:33](=[O:35])[CH:34]=[C:29]([N:25]3[CH2:26][CH2:27][O:28][CH:23]([CH3:22])[CH2:24]3)[N:30]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 97314-FluoroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5360545SodiumHCID 136378672HCID 136378672, compound

Product 1

HCID 136098467HCID 136098467, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

1.46 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride, 6.7 ml of pyridine and 0.7 ml of 4-fluoroaniline are added to a solution of 700 mg of sodium salt of [4-(2-methylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid in 6.7 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 24 hours and then concentrated under reduced pressure. Water and ethyl acetate are added and the resulting mixture is stirred for 30 minutes. The precipitate formed is filtered off and washed with dichloromethane and with ethyl ether, so as to give 300 mg of N-(4-fluorophenyl)-2-[4-(2-methylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide in the form of a white 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 stirred for 30 minutes
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with dichloromethane and with ethyl ether

Sources & evidence

ORD record
ord-6b4263ae2c564ee4b485d6b38705dda7
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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