Dichloromethane → HCID 71811277, compound

HRID 631832Notes

Reaction equation

HRID 631832 reaction equation
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[NH2:16][CH2:17][CH2:18][NH:19][C:20]1[N:24]=[C:23]([N:25]([CH3:27])[CH3:26])[N:22]([CH3:28])[N:21]=1.ClCCl>ClCCl.C(OCC)(=O)C.CN(C=O)C>[CH3:26][N:25]([CH3:27])[C:23]1[N:22]([CH3:28])[N:21]=[C:20]([NH:19][CH2:18][CH2:17][NH:16][C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])[N:24]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 57096144,4,4-Trifluorocrotonic acidHCID 89825611HCID 89825611, compound

Product 1

HCID 71811277HCID 71811277, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-4,4,4-Trifluorobut-2-enoic acid (14 mg, 0.1 mmol) was dissolved in dichloromethane (1 ml containing one drop of dimethyl formamide), oxalyl chloride was added (9 μl, 0.1 mmol) and the solution was stirred at room temperature for 5 minutes. This solution was added to a solution of N3-(2-aminoethyl)-N5,N5,1-trimethyl-1,2,4-triazole-3,5-diamine (18 mg, 0.1 mmol) and TEA (42 μl, 0.3 mmol) in a mixture of anhydrous dichloromethane (1 ml) and anhydrous DMF (1 ml) and the resulting mixture was stirred at room temperature. After one hour, the reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution and brine, dried (magnesium sulfate), concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 5% to 100% acetonitrile) to yield 8 mg of a solid (0.026 mmol, 26%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature
  2. waitAfter one hour
  3. washwashed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 5% to 100% acetonitrile)

Sources & evidence

ORD record
ord-badaa43eda7e458bb0fadc1878ac1f1f
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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