1,2-Dichloroethane → HCID 11649425, compound

HRID 2244967

Reaction equation

HRID 2244967 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH:12]([NH2:16])[C:13]([OH:15])=O)=[CH:3]1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1.[CH3:27][N:28]1[CH2:32][CH2:31][N:30]=[C:29]1[C:33]1[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=1.C(Cl)CCl>CN(C=O)C.O>[CH3:27][N:28]1[CH2:32][CH2:31][N:30]=[C:29]1[C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:13](=[O:15])[CH:12]([CH2:11][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)[NH:16][C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)=[O:26])=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 76934-Chlorophenyl IsocyanateHCID 981121-MethyltryptophanHCID 227288764-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine

Product 1

HCID 11649425HCID 11649425, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of DL-1-methyl-tryptophan (71 mg, 0.33 mmol) in DMF (4 mL), 4-chlorophenyl isocyanate (50 mg, 0.33 mmol) was added. The mixture was then stirred at room temperature overnight. It was filtered. To the filtrate, 4-(1-Methyl-4,5-dihydro-1H-imidazol-2-yl)-phenylamine (150 mg, 0.86 mmol) and H2O (0.5 mL, to solubilize the amine) were added. To the solution, EDC (127 mg, 0.66 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 (108 mg). MS 529.2 and 531.2 (M+H, Cl pattern).

Workup

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

Sources & evidence

ORD record
ord-aaf74f853ba04c9a9f7b0d724e2dd667
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Linked notes

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