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

反応式

HRID 82077 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b387093f535249f8ac46fc3f7dd1f31f
出典データセット
uspto-grants-2014_09
特許番号
US08846714B2

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