Ethylmorpholine → HCID 25094349, compound

HRID 2080999Notes

Reaction equation

HRID 2080999 reaction equation
[CH3:1][N:2]1[CH:6]([C:7]([OH:9])=O)[CH2:5][N:4]([C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)[C:3]1=[O:16].C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:48][C:49]1[C:54]([C:55]([F:58])([F:57])[F:56])=[CH:53][CH:52]=[CH:51][C:50]=1[CH2:59][NH2:60]>ClCCl>[Cl:48][C:49]1[C:54]([C:55]([F:57])([F:58])[F:56])=[CH:53][CH:52]=[CH:51][C:50]=1[CH2:59][NH:60][C:7]([CH:6]1[CH2:5][N:4]([C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)[C:3](=[O:16])[N:2]1[CH3:1])=[O:9]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 52242072-Chloro-3-(trifluoromethyl)benzylamineHCID 67103624HCID 67103624, compound

Product 1

HCID 25094349HCID 25094349, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3-methyl-2-oxo-1-(5-pyrimidinyl)-4-imidazolidinecarboxylic acid (0.6 mmol) in dichloromethane (6 ml) was treated with N-ethyl morpholine (0.460 ml, 3.60 mmol), 1-hydroxybenzotriazole hydrate (110 mg, 0.720 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (138 mg, 0.720 mmol) and the mixture was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (126 mg, 0.600 mmol) in dichloromethane (1 ml) was added and the reaction stirred at room temperature for 3 hours. The mixture was diluted with dichloromethane and the solution was washed with 3N citric acid, water, saturated sodium bicarbonate solution and brine, dried and evaporated. The residue was purified by mass-directed automated HPLC to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(5-pyrimidinyl)-4-imidazolidinecarboxamide (54 mg, 22%). LC/MS [M+H]+=414, retention time 2.37 minutes.

Workup

  1. stirringthe reaction stirred at room temperature for 3 hours
  2. washthe solution was washed with 3N citric acid, water, saturated sodium bicarbonate solution and brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-94a00cb60c2b4dd8b9da8e95e7c1ad91
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

Loading…