Acetic Acid → HCID 22632587, compound

HRID 2417508Notes

Reaction equation

HRID 2417508 reaction equation
[N+:1]([C:4]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:5]=1[CH2:6]C(N)C(OCC)=O)([O-])=O.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1.[CH2:32]([N:34](CC)CC)[CH3:33].[H][H].[N:41]1([C:46]([C:48]2[CH:55]=[CH:54][C:51]([CH:52]=O)=[CH:50][CH:49]=2)=[O:47])[CH2:45][CH:44]=[CH:43][CH2:42]1.C(O)(=[O:58])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C.C(O)C.[OH-].[Na+].[Pd]>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:34]2[CH2:6][C:5]3[CH:14]=[CH:15][C:16]([C:18]([F:19])([F:20])[F:21])=[CH:17][C:4]=3[N:1]([CH2:52][C:51]3[CH:54]=[CH:55][C:48]([C:46]([N:41]4[CH2:45][CH:44]=[CH:43][CH2:42]4)=[O:47])=[CH:49][CH:50]=3)[C:33](=[O:58])[CH2:32]2)=[O:28])=[CH:25][CH:24]=1

Participants

13

Reactant 7

HCID 176Acetic AcidHCID 8471Triethylamine2×HCID 85014-Chlorobenzoyl chlorideHCID 5049666Sodium triacetoxyborohydrideHCID 226325974-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benz-aldehydeHCID 86589880HCID 86589880, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22632587HCID 22632587, compound

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent5×HCID 8857Ethyl AcetateSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

1.6 g (5.2 mmol) of ethyl [2-nitro-4-(trifluoromethyl)benzyl]-aminoacetate was dissolved in 50 ml of dichloromethane. 0.8 ml (6.3 mmol) of 4-chlorobenzoyl chloride and 1.1 ml (7.8 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the crude product was obtained. The crude product was dissolved in a mixture of 10 ml of ethyl acetate and 10 ml of ethanol. 160 mg of 10% palladium/carbon was added to the obtained solution and they were stirred in the presence of hydrogen at room temperature for 4 hours. The reaction mixture was filtered through Celite. The solvent was evaporated and 87 mg (0.21 mmol) of the obtained crude product was dissolved in 10 ml of dichloromethane. 50 mg (0.25 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde and 0.25 ml (0.42 mmol) of acetic acid were added to the obtained solution, and they were stirred at room temperature for 30 minutes. 110 mg (0.53 mmol) of sodium triacetoxyborohydride was added to the reaction mixture, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 5 ml of 1 N sodium hydroxide and 5 ml of ethanol, and the obtained solution was stirred at room temperature for 5 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of dichloromethane. 42 mg (0.25 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.04 ml (0.42 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. The solvent was evaporated, and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. temperatureunder cooling with ice for 2 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. customThe solvent was evaporated
  5. custom87 mg (0.21 mmol) of the obtained crude product
  6. stirringwere stirred at room temperature for 30 minutes
  7. stirringwere stirred at room temperature overnight
  8. stirringthe obtained solution was stirred at room temperature for 5 hours
  9. stirringwere stirred overnight
  10. customThe solvent was evaporated
  11. customthe obtained crude product
  12. additionwas treated in the same manner as in step 3 in Example 1

Sources & evidence

ORD record
ord-5636c485278b45b99db36a40757b2329
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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