1,2-Dichloroethane → HCID 10764654, compound

HRID 1601064Notes

Reaction equation

HRID 1601064 reaction equation
C(Cl)CCl.[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[NH:17][C@@H:16]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=2[CH:25]=1)([OH:7])=O.Cl.Cl.[NH2:28][CH2:29][C:30]1[NH:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1.C1C=CC2N(O)N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[N:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[NH:34][C:30]=1[CH2:29][NH:28][C:5]([C:8]1[CH:9]=[CH:10][C:11]2[NH:17][C@@H:16]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=2[CH:25]=1)=[O:7]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723957(1H-benzo[d]imidazol-2-yl)methanamine dihydrochlorideHCID 15316782HCID 15316782, compound

Product 1

HCID 10764654HCID 10764654, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (1.15 g, 6.02 mmol) was added to a solution of methyl (2S)-7-carboxy-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (2.11 g, 5.02 mmol), 2-aminomethylbenzimidazole dihydrochloride (1.15 g, 6.02 mmol), HOBT.H2O (811 mg, 6.02 mmol), and diisopropylethylamine (1.76 mL, 10 mmol) in anhydrous DMF (25 mL) at RT. After 21 h, the reaction was concentrated on the rotavap (high vacuum), and the residue was taken up in CH2Cl2 (240 mL) and washed with H2O. The organic layer was dried (Na2SO4), dissolved in xylenes, and reconcentrated to remove residual DMF. The crude product was chromatographed on silica gel (MeOH/CHCl3) to give the title compound (1.1 g, 52%).

Workup

  1. customat RT
  2. concentrationthe reaction was concentrated on the rotavap (high vacuum)
  3. washwashed with H2O
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. dissolutiondissolved in xylenes
  6. customto remove residual DMF
  7. customThe crude product was chromatographed on silica gel (MeOH/CHCl3)

Sources & evidence

ORD record
ord-9224614b0a0041bc8df724a16d212755
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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