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Triethylamine → HCID 23153505, compound

HRID 492824
Notes
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Reaction equation

HRID 492824 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:29])[CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH2:27])[CH:22]=3)=[C:16]([F:28])[CH:15]=2)=[O:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:37]1([C:40](Cl)=[O:41])[CH2:39][CH2:38]1.[OH-].[Na+]>CN(C)C=O.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:40]([CH:37]4[CH2:39][CH2:38]4)=[O:41])[CH:22]=3)=[C:16]([F:28])[CH:15]=2)=[O:12])=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 77637Cyclopropanecarbonyl chlorideHCID 23153333N-(4-Fluorophenyl)-N'-[4-(2-aminopyridin-4-yloxy)-3-fluorophenyl]malonamide

Product 1

HCID 23153505HCID 23153505, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 6228DimethylformamideSolvent

Procedure

N-(4-Fluorophenyl)-N′-[4-(2-aminopyridin-4-yloxy)-3-fluorophenyl]malonamide (34 mg) was dissolved in N,N-dimethylformamide (0.5 ml), and then triethylamine (0.047 ml) and cyclopropanecarbonyl chloride (0.016 ml) were added dropwise thereto under a nitrogen atmosphere at room temperature, followed by stirring for 1 hr. To the reaction mixture were added a 1 N aqueous solution of sodium hydroxide (1.5 ml) and methanol (1.0 ml), followed by stirring and extracting with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of ammonium chloride in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (FUJI Silysia NH, eluent; ethyl acetate). Fractions containing the target compound were concentrated to give a residue, which was then dried in vacuum to provide the titled compound (21.1 mg, 53%) as white powder.

Workup

  1. customat room temperature
  2. stirringby stirring
  3. extractionextracting with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of ammonium chloride in this order, and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (FUJI Silysia NH, eluent; ethyl acetate)
  9. additionFractions containing the target compound
  10. concentrationwere concentrated
  11. customto give a residue, which
  12. customwas then dried in vacuum

Sources & evidence

ORD record
ord-b1550135e24e4429975e07267935a9ac
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531532B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes