Ethylenediamine → N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246567노트

반응식

HRID 246567 반응식
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH3:26])[N:18]=3)=[CH:15][N:16]=[C:11]2[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N)CN.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CN(C=O)C.ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH3:26])[N:18]=3)=[CH:15][N:16]=[C:11]2[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 71280190N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

생성물 1

HCID 71279725N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide수율 9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
60 °C

실험 절차

To a stirred solution of N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (306 mg, 638 μmol) in DMF (15 mL) was added ethylenediamine (1.92 g, 2.15 mL, 31.9 mmol) followed by TBAF (1.91 mL, 1.91 mmol) and the mixture heated at 60° C. under nitrogen for 15 h. The mixture was cooled, diluted with dichloromethane, washed with water and brine, then dried (MgSO4), filtered and concentrated to obtain an oil. This was triturated with water to remove tetrabutylammonium hydroxide, filtered, and the residue purified by chromatography (silica, 5-10% methanol in dichloromethane) to obtain N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (19.2 mg, 55.0 μmol, 9%) as a light yellow powder. MS (M+H)+=350; 1H NMR (DMSO-d6) δ: 9.12 (s, 1H), 8.84 (dd, J=8.2, 1.6 Hz, 1H), 8.70 (dd, J=4.5, 1.5 Hz, 1H), 8.42 (s, 1H), 7.93 (s, 1H), 7.39 (dd, J=8.0, 4.5 Hz, 1H), 4.22 (s, 3H).

후처리

  1. temperatureThe mixture was cooled
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto obtain an oil
  7. customThis was triturated with water
  8. customto remove tetrabutylammonium hydroxide
  9. filtrationfiltered
  10. customthe residue purified by chromatography (silica, 5-10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-51574b93004d4c73a238e384d8f4bba3
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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