1,2-Dichloroethane → HCID 178522446, Verbindung

HRID 1012161

Reaktionsgleichung

Reaktionsgleichung von HRID 1012161
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]([C:11](O)=O)=[N:8][NH:9][CH:10]=1.[Cl:19][C:20]1[N:25]=[CH:24][C:23]([NH2:26])=[C:22]([NH2:27])[CH:21]=1.C(Cl)CCl.C1C=CC2N([OH:41])N=NC=2C=1.CCN(CC)CC>CN(C=O)C>[Cl:19][C:20]1[N:25]=[CH:24][C:23]2[N:26]=[C:11]([C:7]3[C:6]([NH:5][C:4](=[O:41])[C:3]4[C:2]([F:1])=[CH:17][CH:16]=[CH:15][C:14]=4[F:18])=[CH:10][NH:9][N:8]=3)[NH:27][C:22]=2[CH:21]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 8171336-Chloropyridine-3,4-diamineHCID 178524951HCID 178524951, Verbindung

Produkt 1

HCID 178522446HCID 178522446, VerbindungAusbeute 6,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(2,6-difluorobenzylamino)-1H-pyrazole-3-carboxylic acid (100 mg, 0.37 mmol) (Example 16D), 6-chloro-pyridine-3,4-diamine (54 mg, 0.37 mmol), EDC (72 mg, 0.40 mmol), HOBt (57.3 mg, 0.40 mmol) and Et3N (0.075 ml, 0.55 mmol) in DMF (20 ml) was stirred at ambient temperature for 48 h and then partitioned between EtOAc and saturated aqueous sodium bicarbonate and the organic portion dried (MgSO4), filtered and evaporated. The amide intermediate was dissolved in AcOH (3 ml), heated at reflux for 1 h, and then heated in the microwave (150 W) at 160° C. until the reaction was complete. The reaction mixture was allowed to cool, a solid crystallised out, which was filtered and then washed with petroleum ether and dried to give the required product (9 mg). (LC/MS: Rt 2.74, [M+H]+ 375)

Aufarbeitung

  1. custompartitioned between EtOAc and saturated aqueous sodium bicarbonate
  2. dry with materialthe organic portion dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe amide intermediate was dissolved in AcOH (3 ml)
  6. temperatureheated
  7. temperatureat reflux for 1 h
  8. temperatureheated in the microwave (150 W) at 160° C. until the reaction
  9. temperatureto cool
  10. customa solid crystallised out, which
  11. filtrationwas filtered
  12. washwashed with petroleum ether
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3cd9bfea20264e5cb6f277b84ad2b8a7
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977477B2

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