Sodium hydride → 3-(1-(6-Benzyloxy-pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-pyridin-2,6-diamine

HRID 78218ノート

反応式

HRID 78218 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([NH2:13])=[N:8][C:9]([NH2:12])=[CH:10][CH:11]=2)[CH:3]=[N:2]1.[H-].[Na+].[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][N:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:23][C:24]1[N:25]=[CH:26][C:27]([CH2:30][N:1]2[CH:5]=[C:4]([C:6]3[C:7]([NH2:13])=[N:8][C:9]([NH2:12])=[CH:10][CH:11]=3)[CH:3]=[N:2]2)=[CH:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 220096002-(Benzyloxy)-5-(chloromethyl)pyridineHCID 592551723-(1H-pyrazol-4-yl)-pyridine-2,6-diamine

生成物 1

HCID 592552513-(1-(6-Benzyloxy-pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-pyridin-2,6-diamine収率 43%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To an N,N-dimethylformamide (5.00 mL) solution of 3-(1H-pyrazol-4-yl)-pyridine-2,6-diamine (30.0 mg, 0.171 mmol) described in Manufacturing Example 36-1-2 was added sodium hydride (7.52 mg, 0.188 mmol, 60% in oil) on an ice bath (0° C.), which was stirred for 30 minutes at room temperature. Thereafter, 2-benzyloxy-5-chloromethyl-pyridine (59.9 mg, 0.257 mmol) described in Manufacturing Example 191-1-2 was added to the mixture, which was stirred for 30 minutes at room temperature. The reaction mixture was partitioned into ethyl acetate and water. The organic layer was washed with water and a saturated sodium chloride aqueous solution, and dried with anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (27.4 mg, 43.0%).

後処理

  1. additionwas added to the mixture, which
  2. stirringwas stirred for 30 minutes at room temperature
  3. customThe reaction mixture was partitioned into ethyl acetate and water
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride aqueous solution, and dried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-ff1937ed8fdc48aaa85bdf91217a1de4
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

反応ノート

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