Ethylamine → HCID 67090140, compound

HRID 2075442Notes

Reaction equation

HRID 2075442 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](/[CH:24]=[CH:25]/[C:26]2[CH:39]=[CH:38][C:29]([C:30]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[O:31])=[CH:28][CH:27]=2)=[N:16]1.C(N)C.[C:43](N1C=CN=C1)([N:45]1[CH:49]=[CH:48][N:47]=[CH:46]1)=[O:44]>C1COCC1.O>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](/[CH:24]=[CH:25]/[C:26]2[CH:27]=[CH:28][C:29]([C:30]([N:32]3[CH2:37][CH2:36][N:35]([C:43]([N:45]4[CH:49]=[CH:48][N:47]=[CH:46]4)=[O:44])[CH2:34][CH2:33]3)=[O:31])=[CH:38][CH:39]=2)=[N:16]1

Participants

7

Reactant 4

HCID 6341EthylamineHCID 682631,1'-CarbonyldiimidazoleHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 11427553(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanone

Product 1

HCID 67090140HCID 67090140, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of dihydrochloride of Compound 18 (400 mg, 1.09 mmol) in THF (20 mL) was added with ethylamine (177 mg, 2.18 mmol) and 1,1′-carbonyldiimidazole (352 mg, 2.18 mmol), followed by stirring at room temperature for 1.5 hours. The reaction mixture was added with water and was extracted with ethyl acetate. The organic layer was washed with saturated brine, and was dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by preparative thin-layer chromatography (chloroform/acetone=1/1) to obtain Compound 48 (350 mg, 44%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by preparative thin-layer chromatography (chloroform/acetone=1/1)

Sources & evidence

ORD record
ord-b8d204ff104240aa94a5ff6820741f81
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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