Trifluoroacetic acid → 1-[3-(4-Amino-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-3-yl)phenyl]ethanone

HRID 238012

반응식

HRID 238012 반응식
CO[C:3]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:4]=1NC(=O)OC(C)(C)C.[CH:26]1([N:31]2[C:35]3=[N:36][CH:37]=[N:38][C:39]([NH2:40])=[C:34]3[C:33](I)=[N:32]2)[CH2:30]CC[CH2:27]1.C([O-])([O-])=O.[Na+].[Na+].[C:48](O)([C:50](F)(F)F)=[O:49].B(Br)(Br)Br>CCO.COCCOC.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:40][C:39]1[N:38]=[CH:37][N:36]=[C:35]2[N:31]([CH:26]([CH3:27])[CH3:30])[N:32]=[C:33]([C:7]3[CH:8]=[C:3]([C:48](=[O:49])[CH3:50])[CH:4]=[CH:5][CH:6]=3)[C:34]=12

참가 물질

10

반응물 5

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 177502214-(tert-Butoxycarbonylamino)-3-methoxyphenylboronic acid, pinacol esterHCID 223468081-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

생성물 1

HCID 529458451-[3-(4-Amino-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-3-yl)phenyl]ethanone

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 6344Dichloromethane용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

A solution of tert-butyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (200 mg, 0.76 mmol) in EtOH (3.3 ml) was added to a solution of 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA80, 100 mg, 0.30 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80° C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified using silica gel column chromatography [MeOH—CH2Cl2, 5:95] yielding BA81. BA81 was dissolved in 50:50 CH2Cl2:TFA and stirred for one hour at room temperature. The reaction mixture was concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81d. BA81d was dissolved in CH2Cl2 (2 ml) and BBr3 (4 mL, 4 mol) was added slowly with a syringe, while stirring. The reaction was stirred at room temperature for 2 hours then concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81dd.

후처리

  1. temperatureAfter cooling
  2. extractionthe reaction was extracted with saturated NaCl and CH2Cl2
  3. concentrationconcentrated in vacuo
  4. custompurified
  5. customyielding BA81
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. custompurified
  8. customto yield BA81d
  9. stirringThe reaction was stirred at room temperature for 2 hours
  10. concentrationthen concentrated in vacuo
  11. custompurified
  12. customto yield BA81dd

출처 및 근거

ORD 기록
ord-0062667054a6491989a46a21eeea6503
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642604B2

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