Propionyl chloride → HCID 178460002, Verbindung

HRID 45861

Reaktionsgleichung

Reaktionsgleichung von HRID 45861
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:14]=[C:15]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[C:42](Cl)(=[O:45])[CH2:43][CH3:44].[Na]>O1CCCC1>[F:30][C:29]([F:31])([F:32])[C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20]([NH:19][C:15]2[CH:14]=[C:13]([C:9]3[C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:42](=[O:45])[CH2:43][CH3:44])[CH:7]=4)=[CH:12][NH:11][N:10]=3)[CH:18]=[CH:17][CH:16]=2)=[O:21])=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 5360545SodiumHCID 178507322HCID 178507322, Verbindung

Produkt 1

HCID 178460002HCID 178460002, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

35 mg (0.08 mmol) of 1-{3-[4-(2-aminopyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)-phenyl]urea were dissolved in 2 ml of dry tetrahydrofuran and 27 μl (0.16 mmol) of N,N-diisopropylethylamine and 14 μl of propionyl chloride (0.16 mmol) were added consecutively. The mixture was stirred overnight at room temperature, then poured into aqueous sodium hydrogenocarbonate, extracted with dichloromethane, dried over sodium sulphate ed evaporated. Without any further purification the crude was redissolved with 10 mL of methanol and 5 mL of triethylamine were added. After 7 hours at room temperature the solvent was removed in vacuo, the residue partitioned between dichloromethane and water, dried over sodium sulphate and evaporated. After trituration with diethylether, 30 mg (77%) of the title compound were collected by filtration.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialdried over sodium sulphate
  3. customed evaporated
  4. customWithout any further purification the crude
  5. dissolutionwas redissolved with 10 mL of methanol and 5 mL of triethylamine
  6. additionwere added
  7. customAfter 7 hours at room temperature the solvent was removed in vacuo
  8. customthe residue partitioned between dichloromethane and water
  9. dry with materialdried over sodium sulphate
  10. customevaporated
  11. filtrationAfter trituration with diethylether, 30 mg (77%) of the title compound were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-4a7436197f5d4f0e9406f54b23c5a9a5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541575B2

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