1,2-Dichloroethane → HCID 53857458, compound

HRID 1601062Notes

Reaction equation

HRID 1601062 reaction equation
C(Cl)CCl.[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[NH:17][CH: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.[NH2:26][CH2:27][C:28]1[NH:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2.C1C=CC2N(O)N=NC=2C=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:36]=[C:28]1[CH2:27][NH:26][C:5]([C:8]1[CH:9]=[CH:10][C:11]2[NH:17][CH: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 582331(1h-indol-2-ylmethyl)amineHCID 23505570Methyl 7-carboxy-2,3,4,5-tetrahydro-4-methyl-3-oxo-1h-1,4-benzodiazepine-2-acetate

Product 1

HCID 53857458HCID 53857458, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (1.53 g, 7.99 mmol) was added to a solution of methyl (±)-7-carboxy-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (2.13 g, 7.26 mmol), 2-aminomethylindole (1.06 g, 7.26 mmol), HOBT.H2O (1.08 g, 7.99 mmol) and diisopropylethylamine (1.53 mL, 8.71 mmol) in anhydrous DMF (10 mL) at RT. After 20 h the reaction was concentrated on the rotavap (high vacuum). The residue was taken up in EtOAc and washed sequentially with H2O and 10% Na2CO3 (2×30 mL). Drying (MgSO4), concentration, and silica gel chromatography (2% MeOH/CH2Cl2) gave the title compound (1.8 g, 60%): 1H NMR (400 MHz, DMSO-d6) δ 8.56 (t, 1H), 7.95 (s, 1H), 7.59 (s, 1H), 7.56 (d, 1H), 7.43 (d, 1H), 7.33 (d, 1H), 7.01 (t, 1H), 6.93 (t, 1H), 6.55 (d, 1H), 6.33 (br, 1H), 6.25 (s, 1H), 5.49 (d, 1H), 5.14 (t, 1H), 4.56 (d, 2H), 3.82 (d, 1H), 3.61 (s, 3H), 2.92 (s, 3H), 2.75 (dd, 1H), 2.53 (d, 1H); MS(ES) m/e 421.2 (M+H)+.

Workup

  1. customat RT
  2. concentrationAfter 20 h the reaction was concentrated on the rotavap (high vacuum)
  3. washwashed sequentially with H2O and 10% Na2CO3 (2×30 mL)
  4. customDrying
  5. concentration(MgSO4), concentration, and silica gel chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-853588cf91ff484ab573901ed9c7f137
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

Loading…