Ammonium Chloride → N-(5-{[2-({[2-(hydroxymethyl)cyclopropyl]carbonyl}amino)imidazo[1,2-b]pyridazin-6-yl]oxy}-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1668118

반응식

HRID 1668118 반응식
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[CH3:6][N:7]1[C:11]([C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH:38]=[CH:39][C:40]=2[CH3:41])[O:18][C:19]2[CH:20]=[CH:21][C:22]3[N:23]([CH:25]=[C:26]([NH:28][C:29]([CH:31]4[CH2:33][CH:32]4[C:34](OC)=[O:35])=[O:30])[N:27]=3)[N:24]=2)=[O:13])=[CH:10][C:9]([CH3:42])=[N:8]1.[Cl-].[NH4+]>O1CCCC1.C(O)C.C(OCC)(=O)C>[OH:35][CH2:34][CH:32]1[CH2:33][CH:31]1[C:29]([NH:28][C:26]1[N:27]=[C:22]2[CH:21]=[CH:20][C:19]([O:18][C:17]3[CH:38]=[CH:39][C:40]([CH3:41])=[C:15]([NH:14][C:12]([C:11]4[N:7]([CH3:6])[N:8]=[C:9]([CH3:42])[CH:10]=4)=[O:13])[CH:16]=3)=[N:24][N:23]2[CH:25]=1)=[O:30]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57505658HCID 57505658, 화합물

생성물 1

HCID 57505665N-(5-{[2-({[2-(hydroxymethyl)cyclopropyl]carbonyl}amino)imidazo[1,2-b]pyridazin-6-yl]oxy}-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide수율 20%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 21873804Tetrahydrofuran ethanol용매2회

실험 절차

To a suspension of calcium chloride (135 mg, 1.1 mmol) in tetrahydrofuran/ethanol (2/1, 1 mL) was added a solution of sodium borohydride (92 mg, 2.2 mmol) and methyl 2-({[6-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]amino}carbonyl)cyclopropanecarboxylate (180 mg, 0.37 mmol) in tetrahydrofuran/ethanol (2/1, 1 mL), and the mixture was stirred at room temperature for 18 hr. Saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate (×3). Combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→100/0, and then methanol/ethyl acetate=0/100→5/95) to give the title compound (35 mg, 20%) as a white solid.

후처리

  1. extractionthe aqueous layer was extracted with ethyl acetate (×3)
  2. washCombined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→100/0

출처 및 근거

ORD 기록
ord-6509e9f12cff41caa2fd161d87636f40
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044049B2

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