Hydrochloric Acid → HCID 69322639, Verbindung

HRID 29110

Reaktionsgleichung

Reaktionsgleichung von HRID 29110
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CC)CC.[C:27]([NH:31][C:32]1[N:36]2[CH:37]=[CH:38][N:39]=[CH:40][C:35]2=[N:34][C:33]=1[C:41]1[S:42][C:43]([C:46]#[C:47][Si](C)(C)C)=[CH:44][CH:45]=1)([CH3:30])([CH3:29])[CH3:28].Br[C:53]1[CH:57]=[CH:56][S:55][CH:54]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])([O-])=O.[Na+].[Na+].[ClH:82]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C1COCC1.CC(=O)OCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[ClH:82].[C:27]([NH:31][C:32]1[N:36]2[CH:37]=[CH:38][N:39]=[CH:40][C:35]2=[N:34][C:33]=1[C:41]1[S:42][C:43]([C:46]#[C:47][C:53]2[CH:57]=[CH:56][S:55][CH:54]=2)=[CH:44][CH:45]=1)([CH3:30])([CH3:29])[CH3:28]

Komponenten

14

Edukt 7

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 133833-BromothiopheneHCID 2724141Tetrabutylammonium FluorideHCID 69322358Tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

Produkt 1

HCID 69322639HCID 69322639, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 67553Tetrabutylammonium IodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

94 mg (0.5 mmol) of copper(I) iodide, 129 mg (0.5 mmol) of triphenylphosphine, 1.32 ml (9.5 mmol) of NEt3, 701 mg (1.9 mmol) of tetra-n-butyl-ammonium iodide and 173 mg (0.25 mmol) of bis(triphenylphosphine)-palladium(II) chloride were added to a solution of 699 mg (1.9 mmol) of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine (synthesis described in Example 158, part a) and 402 mg (2.5 mmol) of 3-bromo-thiophene in DMF (20 ml). 2.5 ml (2.5 mmol) of a 1M solution of tetra-n-butyl-ammonium fluoride in THF were added dropwise to the reaction solution over a period of 1 h. The mixture was then stirred at 70° C. for 18 h. After cooling to RT, the mixture was diluted with EA and combined with a 0.5M aq. Na2CO3 solution. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. CC (acetonitrile/EA 1:3) was carried out with the group, 912 mg of slightly contaminated product being isolated. 304 mg (0.73 mmol, 38%) of N-tert-butyl-2-(5-(thiophen-3-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride were obtained by hydrochloride precipitation in accordance with the method described in Example 192.

Aufarbeitung

  1. customsynthesis
  2. temperatureAfter cooling to RT
  3. customThe phases were separated
  4. extractionthe aq. phase was extracted with EA
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under a vacuum
  8. custombeing isolated

Quellen und Nachweise

ORD-Eintrag
ord-5307783919b94a76beac18ee0625a35e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420056B2

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