Triethylamine → HCID 58734274, compound

HRID 2080467Notes

Reaction equation

HRID 2080467 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:5]([CH:15]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])=[CH:6][C:7]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])=[N:8][CH:9]=1.C(N(CC)CC)C.[C:41](N1C=CN=C1)(N1C=CN=C1)=[O:42].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O.C(Cl)Cl>[Cl:3][C:4]1[C:5]([CH:15]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)(=[O:25])=[O:26])[C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][CH2:13][NH:14][C:41]2=[O:42])=[N:8][CH:9]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 23114814HCID 23114814, compound

Product 1

HCID 58734274HCID 58734274, compoundYield 99%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

To a methylene chloride solution (5.0 ml) of the N-[5-chloro-4-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridin-2-yl]propane-1,3-diamine dihydrochloride (51 mg, 0.091 mmol) obtained in Example 173 were added triethylamine (51 μl, 0.36 mmol) and 1,1′-carbonyldiimidazole (16.2 mg, 0.10 mmol). The resulting mixture was stirred for 17 hours. To the reaction mixture was added ethyl acetate (80 ml). The resulting mixture was washed with water and brine, dried and concentrated under reduced pressure. The residue thus obtained was dissolved in dimethylformamide (1.0 ml). To the resulting solution was added potassium carbonate (27.2 mg, 0.2 mol), followed by stirring under heat at 50° C. for 24 hours. After cooling to room temperature, water was added to the reaction mixture. The resulting mixture was diluted with ethyl acetate (60 ml). The organic layer obtained by separation was washed with brine, dried and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=1:2) to give the title compound (15 mg, 99%) as a white solid.

Workup

  1. washThe resulting mixture was washed with water and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus obtained
  5. stirringby stirring
  6. temperatureAfter cooling to room temperature
  7. customThe organic layer obtained by separation
  8. washwas washed with brine
  9. customdried
  10. concentrationconcentrated under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified by silica gel chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-182efb358f3d4b0bb56b3e30287e693c
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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