Oxalyl chloride → HCID 71657268, compound

HRID 1049831Notes

Reaction equation

HRID 1049831 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:30](=[O:31])[CH2:29][C:28](=[O:32])[NH:27][C:26]3[C:33]4[C:38]([CH:39]=[CH:40][C:25]2=3)=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C.O1CCCC1.CN(C=O)C>[Cl:1][C:2]1[C:3]([C:4]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[C:30](=[O:31])[CH2:29][C:28](=[O:32])[NH:27][C:26]4[C:33]5[C:38]([CH:39]=[CH:40][C:25]3=4)=[CH:37][CH:36]=[CH:35][CH:34]=5)=[CH:20][CH:19]=2)=[O:6])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

9

Reactant 4

HCID 65578Oxalyl chlorideHCID 762582-Chloronicotinic acidHCID 516892Sodium BicarbonateHCID 1176991675-(4-Aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione

Product 1

HCID 71657268HCID 71657268, compoundYield 61.3%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

2-Chloronicotinic acid (63 mg, 0.4 mmol) was suspended in dry dichloromethane (2 mL), the suspension was added with DMF (0.08 mL) and oxalyl dichloride (0.05 mL, 0.6 mmol), and the mixture was stirred at room temperature for 20 hours. The solvent was evaporated under reduced pressure, and the residue was concentrated twice from dry dichloromethane (1 mL) under reduced pressure. The resultant was added with 5-(4-aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (63 mg, 0.2 mmol) obtained in Example 1, (3), dry tetrahydrofuran (4 mL) and triethylamine (0.11 mL), and the mixture was stirred at room temperature for 22 hours, and then refluxed by heating for 4 hours. This reaction mixture was added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from chloroform to obtain the title compound (56 mg, yield 60%) as pale yellow crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. concentrationthe residue was concentrated twice from dry dichloromethane (1 mL) under reduced pressure
  3. stirringthe mixture was stirred at room temperature for 22 hours
  4. temperaturerefluxed
  5. temperatureby heating for 4 hours
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-59afc9e3a73d47d2869fca29ca36176f
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

Loading…