Hydrochloric Acid → HCID 67772616, 화합물

HRID 1963085노트

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HRID 1963085 반응식
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:20]3[N:21]=[CH:22][C:23](C(O)=O)=[CH:24][C:19]3=[C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]=2[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:36]=2[CH3:42])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.N1C2C(=CC=CC=2)C=CC=1.Cl.O1CCOCC1>[Cu]>[F:41][C:37]1[C:36]([CH3:42])=[C:35]([CH:40]=[CH:39][CH:38]=1)[CH2:34][C:17]1[C:18]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:19]2[CH:24]=[CH:23][CH:22]=[N:21][N:20]2[C:16]=1[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:15]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 312751,4-DioxaneHCID 70663716HCID 70663716, 화합물

생성물 1

HCID 67772616HCID 67772616, 화합물수율 37.3%

시약·촉매·용매 1

HCID 23978Copper촉매

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온도
170 °C

실험 절차

A mixture of the compound of example 8, step 11 (0.057 g, 0.10 mmol), copper powder (0.007 g, 0.10 mmol) and quinoline (0.40 ml) was plunged into an oil bath pre-heated at 170° C. for 1.25 h. After cooling to room temperature and evaporation of the volatiles under reduced pressure, the residue was dissolved in EA (10 ml) and the solution washed with water and brine, dried over magnesium sulfate, filtered and concentrated to dryness. The obtained orange oil was purified by chromatography on silica gel (DCM/MOH, 100:0, then 90:10). The product was dissolved in 2 ml of DCM and a 4 N solution of hydrogen chloride in dioxane (0.25 ml, 0.98 mmol) was added. After stirring at room temperature overnight, the solution was evaporated to dryness. The obtained solid was triturated several times with diethyl ether and dried in vacuo at 50° C. to give 0.016 g of the title compound in the form of [6-(3-fluoro-2-methyl-benzyl)-5-phenyl-pyrrolo[1,2-b]pyridazin-7-yl]-piperazin-1-yl-methanone hydrochloride as an orange solid with the following characteristics:

후처리

  1. customwas plunged into an oil bath
  2. temperatureAfter cooling to room temperature
  3. customevaporation of the volatiles under reduced pressure
  4. dissolutionthe residue was dissolved in EA (10 ml)
  5. washthe solution washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe obtained orange oil was purified by chromatography on silica gel (DCM/MOH, 100:0
  10. dissolutionThe product was dissolved in 2 ml of DCM
  11. customthe solution was evaporated to dryness
  12. customThe obtained solid was triturated several times with diethyl ether
  13. customdried in vacuo at 50° C.

출처 및 근거

ORD 기록
ord-e886f967125e4cdcb6f089d05f6baa21
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415336B2

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