Hydrochloric Acid → HCID 69322639、化合物

HRID 29110

反応式

HRID 29110 の反応式
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]

参加物

14

反応物 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

生成物 1

HCID 69322639HCID 69322639、化合物収率 38%

試薬・触媒・溶媒 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 67553Tetrabutylammonium Iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5307783919b94a76beac18ee0625a35e
出典データセット
uspto-grants-2008_09
特許番号
US07420056B2

関連ノート

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