2,4-Dichlorobenzylamine → HCID 25098284, compound

HRID 2080989Notes

Reaction equation

HRID 2080989 reaction equation
OC(C(F)(F)F)=O.[CH3:8][N:9]1[CH:13]([C:14]([OH:16])=O)[CH2:12][N:11]([C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C:10]1=[O:23].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N1CCOCC1)C.[Cl:55][C:56]1[CH:61]=[C:60]([Cl:62])[CH:59]=[CH:58][C:57]=1[CH2:63][NH2:64]>ClCCl>[Cl:55][C:56]1[CH:61]=[C:60]([Cl:62])[CH:59]=[CH:58][C:57]=1[CH2:63][NH:64][C:14]([CH:13]1[CH2:12][N:11]([C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C:10](=[O:23])[N:9]1[CH3:8])=[O:16]

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 131728808HCID 131728808, compound

Product 1

HCID 25098284HCID 25098284, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-methyl-2-oxo-1-(2-pyrimidinyl)-4-imidazolidinecarboxylic acid TFA salt (168 mg, 0.5 mmol), 1-hydroxybenzotriazole hydrate (101 mg, 0.75 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg, 0.75 mmol) and N-ethyl morpholine (0.316 ml, 2.5 mmol) in dichloromethane (8 ml) was stirred at room temperature for 10 minutes. A solution of [1-(2,4-dichlorophenyl)methyl]amine (0.067 ml, 0.5 mmol) in dichloromethane (2 ml) was added and the reaction stirred at room temp for 4 hours. The mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate, The organic phase was separated, washed with water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 0-10% methanol in dichloromethane to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-2-oxo-1-(2-pyrimidinyl)-4-imidazolidinecarboxamide (20 mg, 10.5% yield). LC/MS [M+H]+=380, retention time=2.22 minutes.

Workup

  1. stirringthe reaction stirred at room temp for 4 hours
  2. customThe mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate
  3. customThe organic phase was separated
  4. washwashed with water and brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-a2190533e14946aab09add0db2649c7b
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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