Sodium Carbonate → 3-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4,5-dihydrothiazol-2-yl)benzamide

HRID 237945

반응식

HRID 237945 반응식
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[NH:6][C:7]([C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1)=[O:8].I[C:19]1[C:27]2[C:22](=[N:23][CH:24]=[N:25][C:26]=2[NH2:28])[N:21]([CH:29]([CH3:31])[CH3:30])[N:20]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO.COCCOC.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>[NH2:28][C:26]1[N:25]=[CH:24][N:23]=[C:22]2[N:21]([CH:29]([CH3:31])[CH3:30])[N:20]=[C:19]([C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[C:7]([NH:6][C:2]3[S:1][CH2:5][CH2:4][N:3]=3)=[O:8])[C:27]=12

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 249053373-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 44119636(3-((4,5-Dihydrothiazol-2-yl)carbamoyl)phenyl)boronic acid

생성물 1

HCID 249051543-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4,5-dihydrothiazol-2-yl)benzamide수율 67%

시약·촉매·용매 3

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

반응 조건

온도
80 °C

실험 절차

A solution of [3-((4,5-dihydrothiazol-2-yl)carbamoyl)phenyl]boronic acid (19 mg, 0.08 mmol) in EtOH (3.3 mL) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (20 mg, 0.07 mmol) in DME (12 mL). Pd(PPh3)4 (16 mg, 0.014 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 by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA30 (17.8 mg, 67% yield).

후처리

  1. temperatureAfter cooling
  2. extractionthe reaction was extracted with saturated NaCl and CH2Cl2
  3. concentrationconcentrated in vacuo
  4. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

출처 및 근거

ORD 기록
ord-33dc6e0d69db46f8bea97d77cb704573
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642604B2

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