3,4-Diaminopyridine → 3-(3H-imidazo[4,5-c]pyridin-2-yl)-5-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 82077

반응식

HRID 82077 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[C:16]([CH:17]=O)=[N:15][N:14]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[C:11]2=[N:12][CH:13]=1.[NH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[NH2:32].[S]>CN(C=O)C>[N:32]1[C:31]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[NH:25][C:17]=1[C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[CH:9]=2)[N:14]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[N:15]=1

참가 물질

5

반응물 3

HCID 59183,4-DiaminopyridineHCID 5362487SulfurHCID 583780785-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde

생성물 1

HCID 1361935913-(3H-imidazo[4,5-c]pyridin-2-yl)-5-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde (LVII) (0.120 g, 0.37 mmol), 3,4-diaminopyridine (LVIII) (42 mg, 0.39 mmol) and sulfur (13 mg, 0.39 mmol) in dry DMF (5 mL) was heated at 140° C. under nitrogen for 12 h. The solution was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM and washed with water (1×20 mL). The organic layer was dried over MgSO4, filtered and concentrated to yield 3-(3H-imidazo[4,5-c]pyridin-2-yl)-5-(4-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine (LIX). The crude product was used directly for step 3 without further purification. ESIMS Found for C23H21N7O m/z 412.7 (M+H).

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with water (1×20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b387093f535249f8ac46fc3f7dd1f31f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846714B2

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