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Methanesulfonic Acid → 6-Amino-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522347
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HRID 1522347 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]2[CH:26]=[N:25][N:24]([CH:27]([CH3:29])[CH3:28])[C:16]=2[N:17]=[C:18]([NH:20]CC=C)[CH:19]=1)=[O:13].CS(O)(=O)=O>C(O)C.C(Cl)Cl.[Pd]>[NH2:20][C:18]1[CH:19]=[C:14]([C:12]([NH:11][CH2:10][C:3]2[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[O:13])[C:15]2[CH:26]=[N:25][N:24]([CH:27]([CH3:29])[CH3:28])[C:16]=2[N:17]=1
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참가 물질

6

반응물 2

HCID 6395Methanesulfonic AcidHCID 56597559N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(2-propen-1-ylamino)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

생성물 1

HCID 565975586-Amino-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

시약·촉매·용매 3

HCID 23938Palladium촉매
HCID 702
Ethanol
용매
HCID 6344Dichloromethane용매

실험 절차

A mixture of 10% Pd/C (0.200 g, 0.188 mmol) and N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(2-propen-1-ylamino)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.200 g, 0.507 mmol) was suspended in ethanol (10 mL) and stirred. Added next was methanesulfonic acid (0.033 mL, 0.507 mmol), and the stirring contents were heated at reflux for 2 h. After cooling to room temperature, the reaction mixture was diluted with DCM and filtered through Celite. The filter pad was washed with 10% MeOH/DCM. The filtrate was pre-adsorped onto silica gel, and the crude product purified by silica gel chromatography (dry loaded, eluent: gradient of 5-80% Dichloromethane/Chloroform containing 10% 2M Ammonia (in methanol)). The collected product was dried in vacuum oven at 45° C. overnight. The final product was collected as 0.065 g (36%). LCMS E-S (M+H)=355.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (d, J=6.82 Hz, 6 H), 2.12 (s, 3 H), 2.21 (s, 3 H), 4.31 (d, J=5.05 Hz, 2 H), 4.85-5.00 (m, 1 H), 5.89 (s, 1H), 6.49-6.68 (m, 3 H), 7.85 (s, 1 H), 8.46 (t, J=5.05 Hz, 1 H), 11.54 (br. s., 1 H).

후처리

  1. additionAdded next
  2. temperaturethe stirring contents were heated
  3. temperatureat reflux for 2 h
  4. filtrationfiltered through Celite
  5. washThe filter pad was washed with 10% MeOH/DCM
  6. customthe crude product purified by silica gel chromatography (dry loaded, eluent: gradient of 5-80% Dichloromethane/Chloroform containing 10% 2M Ammonia (in methanol))
  7. customThe collected product was dried in vacuum oven at 45° C. overnight
  8. customThe final product was collected as 0.065 g (36%)

출처 및 근거

ORD 기록
ord-1f2ff11d17ae40a5a6e86651615a85e2
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073924B2

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