Trifluoroacetic acid → 5-[2-(2-Iodobenzoyl)aminoethyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione

HRID 1049735Notes

Reaction equation

HRID 1049735 reaction equation
C(O[C:6]([NH:8][CH2:9][CH2:10][N:11]1[C:17](=[O:18])[CH2:16][C:15](=[O:19])[NH:14][C:13]2[C:20]3[C:25]([CH:26]=[CH:27][C:12]1=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].[I:40][C:41]1[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=1C(Cl)=O>ClCCl>[I:40][C:41]1[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=1[C:6]([NH:8][CH2:9][CH2:10][N:11]1[C:17](=[O:18])[CH2:16][C:15](=[O:19])[NH:14][C:13]2[C:20]3[C:25]([CH:26]=[CH:27][C:12]1=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:7]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 691122-Iodobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 1176992575-[2-(tert-Butoxycarbonyl)aminoethyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione

Product 1

HCID 1176991255-[2-(2-Iodobenzoyl)aminoethyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dioneYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-[2-(tert-Butoxycarbonyl)aminoethyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (16 mg, 0.043 mmol) was dissolved in dichloromethane (4 mL), the solution was added with trifluoroacetic acid (0.1 mL), and the mixture was stirred at room temperature for 19 hours. This reaction mixture was added with saturated aqueous sodium hydrogencarbonate (8 mL) with stirring under ice cooling, and the mixture was stirred for 5 minutes. Further, the mixture was added with 2-iodobenzoyl chloride (0.22 mmol) dissolved in dichloromethane (4 mL) with stirring under ice cooling. This reaction mixture was stirred under ice cooling for 30 minutes, and then at room temperature for 30 minutes. The dichloromethane layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (methanol/chloroform=1/50), and then recrystallized from ethyl acetate/hexane to give the title compound (9 mg, yield 42%) as white crystals. The structure was confirmed by NMR and MS.

Workup

  1. stirringwith stirring under ice cooling
  2. stirringthe mixture was stirred for 5 minutes
  3. stirringwith stirring under ice cooling
  4. stirringThis reaction mixture was stirred under ice cooling for 30 minutes
  5. waitat room temperature for 30 minutes
  6. washThe dichloromethane layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography (methanol/chloroform=1/50)
  10. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5e050a5e69eb4bfdba326ac4ee618f03
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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