Ammonium Chloride → 6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehyde

HRID 2279168노트

반응식

HRID 2279168 반응식
CON(C)[C:4]([C:6]1[C:7]2[C:29]([CH3:30])=[N:28][N:27]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C:8]=2[N:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][C:13]=2[F:26])[CH:11]=1)=[O:5].C[Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[N:9]=[C:8]3[N:27]([CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][O:32]4)[N:28]=[C:29]([CH3:30])[C:7]3=[C:6]([CH:4]=[O:5])[CH:11]=2)=[C:13]([F:26])[CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 900139076-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 900301886-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehyde수율 113.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide (1.0 g) was dissolved in THF (25 mL). At 0° C. methylmagnesium bromide solution (1 M, 3.9 mL) was added slowly, the mixture was warmed to r.t. while stirring overnight. Saturated ammonium chloride solution was added, the mixture was extracted with dichloromethane, the organic phases were dried over magnesium sulfate and concentrated in a membrane pump vacuum. The residue was purified by fish chromatography (silica, heptane/ethyl acetate gradient) giving 1-[6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone (1.0 g, quantitative yield with impurities).

후처리

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in a membrane pump vacuum
  4. customThe residue was purified by fish chromatography (silica, heptane/ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-2b699af02f5e405192059cc52b65d73b
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133181B2

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