Triethylamine → HCID 58865961, compound

HRID 1010836Notes

Reaction equation

HRID 1010836 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH2:9])=[O:8].C(N(CC)CC)C.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([F:27])=[C:22]([CH:26]=1)[C:23](Cl)=[O:24].CO.C(Cl)(Cl)Cl>C(#N)C.C(Cl)(Cl)Cl>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([F:27])=[C:22]([CH:26]=1)[C:23]([NH:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH2:9])=[O:8])=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27736045-Chloro-2-fluorobenzoyl chlorideHCID 104191801-Amino-1H-pyrrole-2-carboxamideHCID 21584188Chloroform methanol

Product 1

HCID 58865961HCID 58865961, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

1-Amino-1H-pyrrole-2-carboxylic acid amide (1.25 g, 10 mmole) was partially dissolved in 45 ml acetonitrile, triethylamine (1.39 ml, 10 mmole) was added followed by dropwise addition of 5-chloro-2-fluorobenzoyl chloride (1.93 g, 10 mmole) in 3 ml chloroform. The reaction mixture was stirred at room temperature overnight, the solvent was removed under vacuum and the residue was taken up in chloroform, washed with 10% sodium bicarbonate, water, and dried over sodium sulfate (anh.). A solid crystallized from solution upon standing. Additional product was obtained by chromatographing the filtrate on silica gel eluting with 3% methanol/chloroform. 600 mg of product was obtained (yield: 21%).

Workup

  1. customthe solvent was removed under vacuum
  2. washwashed with 10% sodium bicarbonate, water
  3. dry with materialdried over sodium sulfate (anh.)
  4. customA solid crystallized from solution
  5. customAdditional product was obtained

Sources & evidence

ORD record
ord-5af8ca3891d04e47a79f0f55be85bb8a
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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