4-Fluoroaniline → HCID 136098480, compound

HRID 2278538Notes

Reaction equation

HRID 2278538 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[Na].[CH2:22]([CH:24]1[O:29][CH2:28][CH2:27][N:26]([C:30]2[N:31]=[C:32]([CH2:37][C:38](O)=[O:39])[NH:33][C:34](=[O:36])[CH:35]=2)[CH2:25]1)[CH3:23]>CN(C)C=O.N1C=CC=CC=1>[CH2:22]([CH:24]1[O:29][CH2:28][CH2:27][N:26]([C:30]2[N:31]=[C:32]([CH2:37][C:38]([NH:6][C:5]3[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=3)=[O:39])[NH:33][C:34](=[O:36])[CH:35]=2)[CH2:25]1)[CH3:23]

Participants

7

Reactant 4

HCID 97314-FluoroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5360545SodiumHCID 136378676HCID 136378676, compound

Product 1

HCID 136098480HCID 136098480, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

4 ml of pyridine, 472 mg of 4-fluoroaniline and 815 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 410 mg of the sodium salt of [4-(2-ethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid in 4 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 16 hours, and then concentrated under reduced pressure. The residue is taken up in 25 ml of water and then the pH is brought back to about 7 with a 2M hydrochloric acid solution. 30 ml of ethyl acetate are added and then the resulting mixture is allowed to stir at ambient temperature for 1 hour. The precipitate formed is filtered off, and then rinsed successively with water and diethyl ether. 300 mg of (±)-2-[4-(2-ethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]-N-(4-fluorophenyl)-acetamide are thus obtained in the form of an off-white powder, the characteristics of which are the following:

Workup

  1. concentrationconcentrated under reduced pressure
  2. addition30 ml of ethyl acetate are added
  3. stirringto stir at ambient temperature for 1 hour
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed successively with water and diethyl ether

Sources & evidence

ORD record
ord-3d13cecd0eb14edb90ad0b180b23f49c
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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