1,2-Dichloroethane → HCID 11620521, compound

HRID 2244966Notes

Reaction equation

HRID 2244966 reaction equation
[NH2:1][CH:2]([C:13]([OH:15])=O)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1.[CH3:26][N:27]1[CH2:31][CH2:30][N:29]=[C:28]1[C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1.C(Cl)CCl>CN(C=O)C.O>[CH3:26][N:27]1[CH2:31][CH2:30][N:29]=[C:28]1[C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:13](=[O:15])[CH:2]([CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)[NH:1][C:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=2)=[O:25])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1148Dl-TryptophanHCID 76934-Chlorophenyl IsocyanateHCID 227288764-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine

Product 1

HCID 11620521HCID 11620521, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of DL-tryptophan (102 mg, 0.50 mmol) in DMF (6 mL), 4-chlorophenyl isocyanate (77 mg, 0.50 mmol) was added. The mixture was then stirred at room temperature overnight. To the reaction mixture, 4-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine (180 mg, 1.02 mmol) and H2O (1 mL, to solubilize the amine) were added. To the solution, EDC (200 mg, 1.04 mmol) was added. After being stirred at room temperature overnight, the solution was concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a powder (200 mg). MS 515.2 and 517.2 (M+H, Cl pattern).

Workup

  1. additionwere added
  2. stirringAfter being stirred at room temperature overnight
  3. concentrationthe solution was concentrated in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-5770b99b09984e0896e7e31f5bd6a6e2
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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