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Water → (R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

HRID 62464
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인쇄 미리보기

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HRID 62464 반응식
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])[N:4]([C@@H:23]2[CH2:31][CH2:30][CH2:29][C:28]3[N:27]([S:32]([C:35]4[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=4)(=[O:34])=[O:33])[N:26]=[CH:25][C:24]2=3)[N:3]=1.CC1(C)C(C)(C)OB([C:50]2[CH:68]=[CH:67][C:53]([C:54]([NH:56][C:57]3[CH:62]=[C:61]([C:63]([F:66])([F:65])[F:64])[CH:60]=[CH:59][N:58]=3)=[O:55])=[CH:52][CH:51]=2)O1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][O:21][C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=1[CH2:12][NH:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([C@@H:23]3[CH2:31][CH2:30][CH2:29][C:28]4[N:27]([S:32]([C:35]5[CH:36]=[CH:37][C:38]([CH3:39])=[CH:40][CH:41]=5)(=[O:33])=[O:34])[N:26]=[CH:25][C:24]3=4)[N:3]=[C:2]([C:50]3[CH:68]=[CH:67][C:53]([C:54]([NH:56][C:57]4[CH:62]=[C:61]([C:63]([F:64])([F:65])[F:66])[CH:60]=[CH:59][N:58]=4)=[O:55])=[CH:52][CH:51]=3)[C:10]=12
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참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 712227974-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamideHCID 90303936(R)-3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

생성물 1

HCID 90304124
(R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide
수율 87.4%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
90 °C

실험 절차

The mixture of (R)-3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (80 mg, 0.125 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (59 mg, 0.150 mmol), Pd(PPh3)2Cl2 (9.2 mg, 0.0125 mmol) and K2CO3 (43 mg, 0.313 mmol) in dioxane/H2O (3 mL/0.3 mL) was stirred for 2 h at 90° C. under nitrogen atmosphere. Then the mixture was added water and extracted with DCM. The combined organic layer was washed with water, brine and dried over anhydrous Na2SO4. Concentrated in vacuo and the residue was purified with silica gel chromatography with PE/EA=1/1 to give (R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (90 mg, yield 87.2%) as yellow solid.

후처리

  1. extractionextracted with DCM
  2. washThe combined organic layer was washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationConcentrated in vacuo
  5. customthe residue was purified with silica gel chromatography with PE/EA=1/1

출처 및 근거

ORD 기록
ord-3612400dd06b457aa0aa1ba65c855177
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09446130B2

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