Potassium Iodide → 2-(2-(3-(Trifluoromethyl)-4,5,6,7-tetrahydroindazole-1-yl)propanamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162750
[F:1][C:2]([F:13])([F:12])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[NH:5][N:4]=1.[H-].[Na+].[I-].[K+].Cl[CH2:19][CH2:20][C:21]([NH:23][C:24]1[S:28][C:27]2[CH2:29][CH2:30][CH2:31][CH2:32][C:26]=2[C:25]=1[C:33]([NH2:35])=[O:34])=[O:22]>CN(C=O)C.O>[F:13][C:2]([F:1])([F:12])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([CH:20]([CH3:19])[C:21]([NH:23][C:24]2[S:28][C:27]3[CH2:29][CH2:30][CH2:31][CH2:32][C:26]=3[C:25]=2[C:33]([NH2:35])=[O:34])=[O:22])[N:4]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 16663982-(3-Chloropropanamido)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamideHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

Produkt 1

HCID 686478992-(2-(3-(Trifluoromethyl)-4,5,6,7-tetrahydroindazole-1-yl)propanamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-(trifluoromethyl)-4,5,6,7-tetrahydroindazole (50 mg, 0.263 mmol) was dissolved in DMF (2 mL). NaH (60% [w/w] suspension in oil, 11 mg, 0.275 mmol) was added followed by potassium iodide (2 mg, catalyst) and the reaction mixture stirred at RT for 30 min. 2-(3-chloropropanamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (75 mg, 0.262 mmol) was then added and the reaction mixture heated at 120° C. for 400 sec in a Biotage SmithCreator microwave. Water was added followed by EtOAc (3×10 mL) extraction. The EtOAc layers were washed with water (5×5 mL), brine, dried over MgSO4, filtered and the solvent removed in vacuo to give a yellow gum. Purification by preparative reverse phase HPLC gave desired product (22.7 mg, 0.052 mmol, 20%).

Aufarbeitung

  1. temperaturethe reaction mixture heated at 120° C. for 400 sec in a Biotage SmithCreator microwave
  2. extractionfollowed by EtOAc (3×10 mL) extraction
  3. washThe EtOAc layers were washed with water (5×5 mL), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customto give a yellow gum
  8. customPurification by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9fcb980c4b0c40ada260e2c055f276c5
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820707B2

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