Oxalyl chloride → HCID 71811871, compound

HRID 631811Notes

Reaction equation

HRID 631811 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.[CH3:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]([NH:26][CH2:27][CH2:28][NH2:29])[CH:18]=1.CCOP(O)N(C(C)C)C(C)C>ClCCl>[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5]([NH:29][CH2:28][CH2:27][NH:26][C:19]1[CH:18]=[C:17]([CH3:16])[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=1)=[O:6]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 1954513'-O-ethyl-N,N-diisopropylphosphoramiditeHCID 57096144,4,4-Trifluorocrotonic acidHCID 22142401(2-Aminoethyl)(4-methyl-5-nitro(2-pyridyl))amine

Product 1

HCID 71811871HCID 71811871, compoundYield 5.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 6344DichloromethaneSolvent

Procedure

(E)-4,4,4-Trifluorobut-2-enoic acid (32 mg, 0.23 mmol) was dissolved in dichloromethane (0.5 ml containing one drop of dimethyl formamide), oxalyl chloride was added (23 μl, 0.23 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of N-(4-methyl-5-nitro-2-pyridyl)ethane-1,2-diamine (29 mg, 0.15 mmol) and EDIPA (70 μl, 0.5 mmol) in anhydrous dichloromethane (2 ml) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile) to yield 2.4 mg of a solid (0.0076 mmol, 5% yield).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 10% to 100% acetonitrile)

Sources & evidence

ORD record
ord-67b4bac13a5d43cf849258dd613a5efc
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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