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Dimethylformamide → N-(4-fluorophenyl)-N-(6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-yl)cyclopropane-1,1-dicarboxamide

HRID 2241209
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HRID 2241209 반응식
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[N:23]=[CH:22][C:21](N)=[CH:20][CH:19]=4)=[C:11]3[C:10]([CH3:25])=[N:9]2)=[CH:5][CH:4]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([C:38]2([C:41](F)=[O:42])[CH2:40][CH2:39]2)=[O:37])=[CH:31][CH:30]=1.C[N:45](C=O)C.CCN(C(C)C)C(C)C>O>[F:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]([C:21]2[CH:22]=[N:23][C:18]([O:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]4[N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=5)[N:9]=[C:10]([CH3:25])[C:11]=34)=[CH:19][CH:20]=2)[C:36]([C:38]2([C:41]([NH2:45])=[O:42])[CH2:40][CH2:39]2)=[O:37])=[CH:31][CH:30]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 685181536-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-amineHCID 866146491-((4-Fluorophenyl)carbamoyl)cyclopropanecarbonyl fluoride

생성물 1

HCID 68512422N-(4-fluorophenyl)-N-(6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-yl)cyclopropane-1,1-dicarboxamide
수율 59%

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

A 100 mL round-bottomed flask was charged with 6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-amine (0.500 g, 1.38 mmol), 1-((4-fluorophenyl)carbamoyl)cyclopropanecarbonyl fluoride (0.545 g, 2.42 mmol; prepared as in Example 6, Step A), and DMF (10 mL). DIEA (0.723 mL, 4.15 mmol) was added under nitrogen and the reaction mixture was heated at 50° C. for 18 hours. The reaction mixture was cooled to room temperature, diluted with water (100 mL), and extracted with EtOAc (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to provide the crude product (1.55 g, 59%). LRMS (esi+) 567 (M+H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (50 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f55968349cd04124a965ba67263ed607
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723330B2

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