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Diisopropylethylamine → 6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-phenyl-piperidin-4-yl)-amide

HRID 2360700
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HRID 2360700 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:31](O)=[O:32])[C:18]3[C:23]([CH3:24])=[N:22][N:21]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[C:19]=3[N:20]=2)=[C:11]([F:34])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][CH2:36][N:37]([CH:41]([CH3:43])C)[CH:38]([CH3:40])C>ClC(Cl)C>[CH2:41]([N:37]1[CH2:36][CH2:35][C:15]([NH:20][C:31]([C:17]2[C:18]3[C:23]([CH3:24])=[N:22][N:21]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[C:19]=3[N:20]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:10][C:11]=3[F:34])[CH:16]=2)=[O:32])([C:12]2[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=2)[CH2:40][CH2:38]1)[C:43]1[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 81531DiisopropylethylamineHCID 866803216-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

생성물 1

HCID 866803236-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-phenyl-piperidin-4-yl)-amide수율 59%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

A mixture of 6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (304 mg), amine (200 (200 mg), DIPEA (340 μL) and BEP (190 mg) in dichloroethane (6.5 mL) was stirred at r.t. for 90 min. The solvent was distilled off in vacuo, the residue was re-dissolved in ethyl acetate (20 mL) and washed twice with water, twice with saturated sodium bicarbonate solution and with brine, then dried over magnesium sulfate. After evaporation of the solvents, the residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient) giving 278 mg (59%) of the title compound.

후처리

  1. distillationThe solvent was distilled off in vacuo
  2. dissolutionthe residue was re-dissolved in ethyl acetate (20 mL)
  3. washwashed twice with water, twice with saturated sodium bicarbonate solution and with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvents
  6. customthe residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-180696ac3cd045dd8264e3401e30896f
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08686150B2

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