Dichloromethane → 1-(6-(6-(2,4-Difluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethanone

HRID 1930086노트

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HRID 1930086 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:18]=[CH:19][C:20]3[N:21]([C:23]([C:26](OCC)=[O:27])=[N:24][N:25]=3)[N:22]=1)[CH:14]=[CH:13][O:12]2.[CH3:31][Mg]Cl.[Cl-].[NH4+].C(Cl)Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:18]=[CH:19][C:20]3[N:21]([C:23]([C:26](=[O:27])[CH3:31])=[N:24][N:25]=3)[N:22]=1)[CH:14]=[CH:13][O:12]2

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 57929910Ethyl 6-(6-(2,4-difluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylateHCID 178418332HCID 178418332, 화합물

생성물 1

HCID 579298721-(6-(6-(2,4-Difluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethanone

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
-30 °C

실험 절차

In a 100 mL round-bottomed flask, ethyl 6-(6-(2,4-difluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate (2.00 g, 4.87 mmol) was suspended in THF (30 mL) and cooled to about −30° C. A solution of methylmagnesium chloride (3 M in THF, 6.50 mL, 19.5 mmol) was added over about 10 min to the suspension. The mixture was stirred for about 25 min at about −30° C., followed by slow addition of a saturated solution of ammonium chloride (15 mL). The suspension was diluted with the addition of water (20 mL) and then DCM (20 mL). The layers were separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic extracts were washed with water and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give a solid that was triturated with Et2O (15 mL) and collected by vacuum filtration as a slightly off-white powder (1.50 g, 81%): LC/MS (Table 1, Method g) Rt=2.06 min; MS m/z: 380.9 (M+H)+.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with DCM (2×50 mL)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customto give a solid
  8. customthat was triturated with Et2O (15 mL)
  9. filtrationcollected by vacuum filtration as a slightly off-white powder (1.50 g, 81%)

출처 및 근거

ORD 기록
ord-5abde91abe434617938a2445239da47c
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188083B2

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