Triethylamine → HCID 86682949, compound

HRID 1497088Notes

Reaction equation

HRID 1497088 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH:3]=1.[CH2:18]([O:20][C:21](=[O:26])[CH2:22][C:23](Cl)=[O:24])[CH3:19].C(N(CC)CC)C>C1COCC1.O>[CH2:18]([O:20][C:21](=[O:26])[CH2:22][C:23]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:9]#[C:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=[O:24])[CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 86682928HCID 86682928, compound

Product 1

HCID 86682949HCID 86682949, compoundYield 62.71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-chloro-2-(2-chloro-phenylethynyl)-phenylamine (prepared as described in example 10 step A, 4 g, 15.26 mmol) in THF (25 ml) at 0° C. was added chlorocarbonyl-acetic acid ethyl ester followed by triethyl amine (3.2 ml, 22.89 mmol) drop wise under nitrogen, then the reaction mixture was stirred for 4 h at 25° C. The reaction mixture was diluted with water (50 ml), and extracted with EtOAc (3×75 ml). The organic phases were combined and washed with brine (40 ml), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (5-10% EtOAc/hexane) to afford N-[4-chloro-2-(2-chloro-phenylethynyl)-phenyl]-malonamic acid ethyl ester (3.6 g, 62.71%) as an off white solid. LC-MS (ESI): 376 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×75 ml)
  2. washwashed with brine (40 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude residue which
  7. customwas purified by flash column chromatography (5-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-83cf941ad8b34b15a08d1a6d8c35b66a
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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