1,2-Dichloroethane → HCID 23218411, compound

HRID 2294876Notes

Reaction equation

HRID 2294876 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH:10]([CH3:12])[CH3:11])[C:6]2[CH:13]=[CH:14][CH:15]=[CH:16][C:5]=2[N:4]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:3]1=[O:22].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:37][C:38]1[CH:39]=[C:40]([CH2:45][C:46](O)=[O:47])[CH:41]=[C:42]([Cl:44])[CH:43]=1>CN(C)C=O.C(OCC)(=O)C>[O:9]=[C:8]1[N:7]([CH:10]([CH3:11])[CH3:12])[C:6]2[CH:13]=[CH:14][CH:15]=[CH:16][C:5]=2[N:4]([CH2:17][C:18]([F:19])([F:21])[F:20])[C:3](=[O:22])[CH:2]1[NH:1][C:46](=[O:47])[CH2:45][C:40]1[CH:39]=[C:38]([Cl:37])[CH:43]=[C:42]([Cl:44])[CH:41]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 64524872-(3,5-Dichlorophenyl)acetic acidHCID 21472089HCID 21472089, compound

Product 1

HCID 23218411HCID 23218411, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 3-amino-1-(2-propyl)-5-(2,2,2-trifluoroethyl)-1,5-benzodiazepine-2,4-dione (180 mg, 0.57 mmol) in N,N-dimethylformamide (2 mL) was added EDC (131 mg, 0.69 mmol), HOBT (46 mg, 0.34 mmol) and 3,5-dichlorophenylacetic acid (140 mg, 0.69 mmol). The reaction was stirred at room temperature for 2 hours. The reaction was diluted with ethyl acetate (50 mL), then washed with 10% aqueous potassium hydrogen sulfate (25 mL) then saturated aqueous sodium hydrogen carbonate (25 mL) and finally, brine (25 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 25-40% ethyl acetate:hexane to give 100 mg of product which was crystallized from ethyl acetate/hexane to give colorless crystals (70 mg). m.p.=185°-186° C.

Workup

  1. washwashed with 10% aqueous potassium hydrogen sulfate (25 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 25-40% ethyl acetate

Sources & evidence

ORD record
ord-6f8ff5092f194bff8eb7f09107f90ade
Source dataset
uspto-grants-1997_11
Patent number
US05691331

Reaction notes

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