Sodium Carbonate → 1-isopropyl-3-(2-(methylamino)benzo[d]thiazol-6-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 880525노트

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HRID 880525 반응식
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:12]([CH3:14])[CH3:13])[N:3]=1.[CH3:15][NH:16][C:17]1[S:18][C:19]2[CH:25]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:23]=[CH:22][C:20]=2[N:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCO.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:12]([N:4]1[C:5]2=[N:6][CH:7]=[N:8][C:9]([NH2:11])=[C:10]2[C:2]([C:24]2[CH:23]=[CH:22][C:20]3[N:21]=[C:17]([NH:16][CH3:15])[S:18][C:19]=3[CH:25]=2)=[N:3]1)([CH3:14])[CH3:13]

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 249053373-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 58279591N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-amine2회

생성물 1

HCID 866537311-isopropyl-3-(2-(methylamino)benzo[d]thiazol-6-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine수율 34.1%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

A mixture of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (104) (47 mg, 0.16 mmol), N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-amine (703 (37 mg, 0.13 mmol), Pd(OAc)2 (6 mg, 0.027 mmol), triphenyl phosphine (20 mg, 0.076 mmol) and Na2CO3 (69 mg, 0.65 mmol) was dissolved in a mixture of DMF (4 mL), EtOH (4 mL) and H2O (2 mL). The resulting mixture was degassed and back-filled with argon three times and then stirred at 90° C. for 1.5 h. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (200-300 mesh) eluting with DCM/MeOH (20/1) to give the desired product 1-isopropyl-3-(2-(methylamino)benzo[d]thiazol-6-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (704) (15 mg, 34.1%) as a pale solid. ESI-MS (M+H)+ m/z: 340.05.

후처리

  1. customThe resulting mixture was degassed
  2. additionback-filled with argon three times
  3. temperatureto cool to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel (200-300 mesh)
  7. washeluting with DCM/MeOH (20/1)

출처 및 근거

ORD 기록
ord-e4061b5f0563459abff8889810b27211
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993580B2

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