Hydrochloric Acid → HCID 69322639, 화합물

HRID 29110

반응식

HRID 29110 반응식
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]

참가 물질

14

반응물 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

생성물 1

HCID 69322639HCID 69322639, 화합물수율 38%

시약·촉매·용매 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 67553Tetrabutylammonium Iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5307783919b94a76beac18ee0625a35e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420056B2

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