3-Hydroxy-3-methyl-butanal → 1-(6-(6-(2,4-Difluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-2-methylpropan-2-ol

HRID 1930095노트

반응식

HRID 1930095 반응식
[OH:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:17]=[C:18]2[N:22]([C:23]=1[C:24]1[N:25]=[N:26][C:27]([NH:30][NH2:31])=[CH:28][CH:29]=1)[CH:21]=[CH:20][O:19]2.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:17]=[C:18]2[N:22]([C:23]=1[C:24]1[CH:29]=[CH:28][C:27]3[N:26]([C:4]([CH2:3][C:2]([CH3:7])([OH:1])[CH3:6])=[N:31][N:30]=3)[N:25]=1)[CH:21]=[CH:20][O:19]2

참가 물질

5

반응물 3

HCID 110515913-Hydroxy-3-methyl-butanalHCID 12217721Iodo benzene diacetateHCID 579298696-(2,4-Difluorophenyl)-5-(6-hydrazinylpyridazin-3-yl)imidazo[2,1-b]oxazole

생성물 1

HCID 498308011-(6-(6-(2,4-Difluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-2-methylpropan-2-ol수율 33.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To round bottom flask, 3-hydroxy-3-methylbutanal (0.178 g, 1.185 mmol) and 6-(2,4-difluorophenyl)-5-(6-hydrazinylpyridazin-3-yl)imidazo[2,1-b]oxazole (0.3 g, 0.859 mmol) and DCM 5 mL were added. The reaction mixture was stirred at about ambient temperature for about 1 h. Iodobenzene diacetate (0.38 g, 1.18 mmol) was added and was stirred at ambient temperature for overnight. The reaction mixture was quenched with water. The aqueous phase was extracted with DCM and the organic layer was concentrated under reduced pressure. The crude material was purified by silica gel chromatography using DCM/MeOH (90:10). After concentration of the fractions with product, the resulting solid was triturated with ether. The solid was collected by filtration then dried under vacuum at about 60° C. for about 2 days to give the title compound (0.118 g, 33.5%): LC/MS (Table 1, Method g) Rt=1.78 min; MS m/z: 411.2 (M+H)+. 1H NMR (DMSO-d6) δ 8.52 (d, 1H), 8.27 (d, 1H), 8.21 (d, 1H), 7.75 (m, 1H), 7.50-7.40 (m, 1H), 7.34-7.25 (m, 1H), 6.90 (m, 1H), 4.71 (s, 1H), 3.33 (s, 2H), 1.27 (s, 6H)

후처리

  1. stirringwas stirred at ambient temperature for overnight
  2. customThe reaction mixture was quenched with water
  3. extractionThe aqueous phase was extracted with DCM
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe crude material was purified by silica gel chromatography
  6. customAfter concentration of the fractions with product, the resulting solid was triturated with ether
  7. filtrationThe solid was collected by filtration
  8. customthen dried under vacuum at about 60° C. for about 2 days

출처 및 근거

ORD 기록
ord-23f8338d970d4a7285caf64f16efb392
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188083B2

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