Triethylamine hydrochloride → 6-Chloro-3-(2,6-difluorophenyl)-7-(1,1-dimethylethyl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 2301337

반응식

HRID 2301337 반응식
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9].[F:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:15]=1[C:16]([NH:18][NH2:19])=O.Cl.C(N(CC)CC)C>O1CCOCC1>[Cl:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]2[N:4]([C:16]([C:15]3[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:14]=3[F:13])=[N:18][N:19]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 11130Triethylamine hydrochlorideHCID 898464-tert-Butyl-3,6-dichloropyridazineHCID 6764492,6-Difluorobenzhydrazide

생성물 1

HCID 183724156-Chloro-3-(2,6-difluorophenyl)-7-(1,1-dimethylethyl)-1,2,4-triazolo[4,3-b]pyridazine수율 13.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A mixture of 3,6-dichloro-4-(1,1-dimethylethyl)pyridazine (2 g, 9.75 mmol), 2,6-difluorobenzoic acid hydrazide (2.52 g, 14.6 mmol) (WO 95/24403) and triethylamine hydrochloride (2.01 g, 14.6 mmol) in 1,4-dioxane (10 ml) was stirred and heated at reflux for 3.5 days. Upon cooling, the volatiles were removed in vacuo and the residue was triturated with dichloromethane. Any undissolved solid was removed by filtration. The residue was purified by chromatography on silica gel eluting with 0%→25% ethyl acetate in dichloromethane to give the required product (0.42 g). Data for the title compound: 1H NMR (250 MHz, CDCl3) δ1.57 (9H, s), 7.09-7.16 (2H, m), 7.51-7.63 (1H, m), 8.19 (1H, s); MS (ES30) m/e 323 (MH+.

후처리

  1. temperatureheated
  2. temperatureat reflux for 3.5 days
  3. temperatureUpon cooling
  4. customthe volatiles were removed in vacuo
  5. customthe residue was triturated with dichloromethane
  6. customAny undissolved solid was removed by filtration
  7. customThe residue was purified by chromatography on silica gel eluting with 0%→25% ethyl acetate in dichloromethane

출처 및 근거

ORD 기록
ord-34c2f76c0c3849799ce74e5dab82164e
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06500828B1

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