Hydrochloric Acid → 1-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt

HRID 386569

반응식

HRID 386569 반응식
[C:1]([C:4]1[C:9]([O:10][CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:8][C:7](=[O:24])[N:6]([C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([F:33])[CH:26]=2)[N:5]=1)(=O)[NH2:2].[ClH:34].O1CCOCC1.CCOCC>C(Cl)Cl>[ClH:34].[C:31]([C:28]1[CH:29]=[CH:30][C:25]([N:6]2[C:7](=[O:24])[CH:8]=[C:9]([O:10][CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:4]([C:1]#[N:2])=[N:5]2)=[CH:26][C:27]=1[F:33])#[N:32]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 67445416tert-Butyl 4-(3-carbamoyl-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate

생성물 1

HCID 674470261-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirring solution of tert-butyl 4-(3-cyano-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate (example 34) (22 mg, 0.050 mmol) in DCM (3 mL) at room temperature under argon was added 4 M HCl in dioxane (0.375 mL, 1.5 mmol). The reaction mixture was stirred at room temperature overnight. Et2O (10 mL) was added to the reaction mixture. The solid product was collected by filtration and further washed with ether (2 mL×2). After drying under vacuum for 2 hours, 19 mg (100%) of 1-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt was obtained as an off-white solid. MS (ESI) 340 (M+H).

후처리

  1. filtrationThe solid product was collected by filtration
  2. washfurther washed with ether (2 mL×2)
  3. customAfter drying under vacuum for 2 hours

출처 및 근거

ORD 기록
ord-736e5b60b2b9431eb66248be4cd7047a
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372837B2

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