2,4-Dichlorobenzylamine → N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-[4-(methyloxy)-2-pyrimidinyl]-2-oxo-4-imidazolidinecarboxamide

HRID 2081048Notes

Reaction equation

HRID 2081048 reaction equation
[CH3:1][N:2]1[CH:6]([C:7]([OH:9])=O)[CH2:5][N:4]([C:10]2[N:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][N:11]=2)[C:3]1=[O:18].C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:50][C:51]1[CH:56]=[C:55]([Cl:57])[CH:54]=[CH:53][C:52]=1[CH2:58][NH2:59]>ClCCl.C(=O)([O-])O.[Na+]>[Cl:50][C:51]1[CH:56]=[C:55]([Cl:57])[CH:54]=[CH:53][C:52]=1[CH2:58][NH:59][C:7]([CH:6]1[CH2:5][N:4]([C:10]2[N:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][N:11]=2)[C:3](=[O:18])[N:2]1[CH3:1])=[O:9]

Participants

8

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 671036213-Methyl-1-[4-(methyloxy)-2-pyrimidinyl]-2-oxo-4-imidazolidinecarboxylic acid

Product 1

HCID 25095697N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-[4-(methyloxy)-2-pyrimidinyl]-2-oxo-4-imidazolidinecarboxamideYield 48.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

3-Methyl-1-[4-(methyloxy)-2-pyrimidinyl]-2-oxo-4-imidazolidinecarboxylic acid (76 mg, 0.3 mmol) (˜0.3 mmol) in dichloromethane (4 ml) was treated with the 4A molecular sieves (200 mg, 0.300 mmol), and the mixture stirred at RT for 5 minutes. N-Ethylmorpholine (0.190 ml, 1.500 mmol), 1-hydroxybenzotriazole hydrate (55.1 mg, 0.360 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (82 mg, 0.360 mmol) were then added and the reaction stirred at RT under argon for 10 minutes. [(2,4-Dichlorophenyl)methyl]amine (58.1 mg, 0.330 mmol) was added and the reaction left to stir at RT under argon for 4 hours. The reaction mixture was diluted with dichloromethane (15 ml) and saturated sodium hydrogen carbonate solution (20 ml), and the product was extracted into dichloromethane (×2). The combined organic extracts were washed with water (20 ml), brine (20 ml) and then dried over magnesium sulphate. The solvent was evaporated in vacuo to give a yellow solid, which was purified by mass-directed automated HPLC. Fractions containing product were combined and solvent evaporated in vacuo, co-evaporated with diethyl ether to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-[4-(methyloxy)-2-pyrimidinyl]-2-oxo-4-imidazolidinecarboxamide as a white solid (60 mg, 46.3% yield). LC/MS [M+H]+=410, retention time 1.73=minutes.

Workup

  1. stirringthe reaction stirred at RT under argon for 10 minutes
  2. waitthe reaction left
  3. stirringto stir at RT under argon for 4 hours
  4. extractionthe product was extracted into dichloromethane (×2)
  5. washThe combined organic extracts were washed with water (20 ml), brine (20 ml)
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was evaporated in vacuo
  8. customto give a yellow solid, which
  9. customwas purified
  10. additionFractions containing product
  11. customsolvent evaporated in vacuo, co-evaporated with diethyl ether

Sources & evidence

ORD record
ord-03c90663eb474397b443d503abe3601e
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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