2,4-Dichlorobenzylamine → HCID 25095701, compound

HRID 2081051Notes

Reaction equation

HRID 2081051 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH:11]([C:13]([OH:15])=O)[N:10]([CH3:16])[C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1.C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:49][C:50]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:51]=1[CH2:57][NH2:58]>ClCCl>[Cl:49][C:50]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:51]=1[CH2:57][NH:58][C:13]([CH:11]1[CH2:12][N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=2)[C:9](=[O:17])[N:10]1[CH3:16])=[O:15]

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67103406HCID 67103406, compound

Product 1

HCID 25095701HCID 25095701, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(2-fluoro-4-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid (200 mg, 0.521 mmol) and N-ethyl morpholine (0.400 ml, 3.13 mmol) in dichloromethane (10 ml) was treated with 1-hydroxybenzotriazole hydrate (80 mg, 0.521 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (100 mg, 0.521 mmol) and the reaction mixture was stirred at room temperature for 10 minutes. [(2,4-Dichlorophenyl)methyl]amine (0.084 ml, 0.521 mmol) was then added and the reaction stirred overnight. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine and separated through a hydrophobic frit. The organic layer was reduced under vacuum. The residue was purified mass-directed automated HPLC to give N-[(2,4-dichlorophenyl)methyl]-1-(2-fluoro-4-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide (64 mg, 30.3% yield). LC/MS [M+H]+=397, retention time=2.45 minutes.

Workup

  1. stirringthe reaction stirred overnight
  2. washwashed with saturated sodium hydrogen carbonate solution, water and brine
  3. customseparated through a hydrophobic frit
  4. customThe residue was purified mass-directed

Sources & evidence

ORD record
ord-c691f9af5b154548bda20a0f013621db
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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