1,2-Dichloroethane → HCID 54392167, compound

HRID 1106922Notes

Reaction equation

HRID 1106922 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([CH2:9][N:10]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16](=[O:23])[CH2:15][CH2:14][N:13]([C:24](=[O:33])[NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)[CH2:12][C:11]1=[O:34])(O)=[O:7].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH3:32][C:28]1[CH:27]=[C:26]([NH:25][C:24]([N:13]2[CH2:14][CH2:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:10]([CH2:9][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[C:11](=[O:34])[CH2:12]2)=[O:33])[CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 18788126HCID 18788126, compound

Product 1

HCID 54392167HCID 54392167, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Pyrrolidine (117 μl, 1.41 mmol) was added to a solution of 1-carboxymethyl-4-(3-methylphenyl)carbamyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonin(373 mg, 0.94 mmol), EDC (181 mg, 0.94 mmol) and HOBt (127 mg, 0.94 mmol) in DMF (3 ml) at room temperature. The reaction mixture was stirred at room temperature for 28 hours, diluted with water (50 ml), and extracted with ethyl acetate (50 ml). The organic extract was washed with 10% citric acid solution (50 ml), brine (2×50 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the crude product which was purified by chromatography on silica gel with ethyl acetate as eluant. (138 mg, 34%).

Workup

  1. extractionextracted with ethyl acetate (50 ml)
  2. extractionThe organic extract
  3. washwas washed with 10% citric acid solution (50 ml), brine (2×50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-8a4660cc4e004846b04c8ccd00f8a3fc
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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