Triethylamine → HCID 23153448, compound

HRID 492822Notes

Reaction equation

HRID 492822 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)=[CH:16][C:15]=2[F:28])=[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)=[CH:16][C:15]=2[F:28])=[O:12])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 77637Cyclopropanecarbonyl chlorideHCID 23152971HCID 23152971, compound

Product 1

HCID 23153448HCID 23153448, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

N-(4-Fluorophenyl)-N′-[4-(2-aminopyridin-4-yloxy)-2-fluorophenyl]malonamide (21.3 mg) was dissolved in N,N-dimethylformamide (0.5 ml), and then triethylamine (0.030 ml) and cyclopropanecarbonyl chloride (0.010 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 (1.0 ml) and methanol (1.0 ml), followed by stirring and extracting with ethyl acetate. The organic layer was concentrated under a reduced pressure to give a residue, which was 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 (9.6 mg, 39%) as white powder.

Workup

  1. customat room temperature
  2. stirringby stirring
  3. extractionextracting with ethyl acetate
  4. concentrationThe organic layer was concentrated under a reduced pressure
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography (FUJI Silysia NH, eluent; ethyl acetate)
  7. additionFractions containing the target compound
  8. concentrationwere concentrated
  9. customto give a residue, which
  10. customwas then dried in vacuum

Sources & evidence

ORD record
ord-76cb11a771ff4a9fac7d0310a5cfe178
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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