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Cesium carbonate → rac-{1-[({7-[(3-Fluoropyridin-2-yl)methoxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

HRID 1486310
ノート
印刷プレビュー

反応式

HRID 1486310 の反応式
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]([CH3:28])([CH2:25][CH2:26][CH3:27])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:24])=[N:15][N:16]2[C:21]([OH:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=12)=[O:12])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][C:38]1[C:43]([F:44])=[CH:42][CH:41]=[CH:40][N:39]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]([CH3:28])([CH2:25][CH2:26][CH3:27])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:24])=[N:15][N:16]2[C:21]([O:22][CH2:37][C:38]3[C:43]([F:44])=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=12)=[O:12])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 216131732-(Bromomethyl)-3-fluoropyridineHCID 178444850HCID 178444850、化合物

生成物 1

HCID 117864682rac-{1-[({7-[(3-Fluoropyridin-2-yl)methoxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester収率 33%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A solution of 49 mg (0.12 mmol) of rac-[1-{[7-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carbonyl)amino]}-1-methylbutyl)carbamic acid tert-butyl ester (Example 141A) in 2.1 ml of DMF was admixed with 78 mg (0.24 mmol) of caesium carbonate and 69 mg (0.360 mmol) of 2-bromomethyl-3-fluoropyridine (Example 143A). The reaction mixture was stirred at room temperature for 18 hours. The solvent was evaporated off under reduced pressure and the residue was partitioned between dichloromethane and water. The organic phase was removed and concentrated under reduced pressure. The residue was purified by preparative HPLC chromatography (Method 21), which gave 21 mg (33% yield, 96% pure) of the target compound.

後処理

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe residue was partitioned between dichloromethane and water
  3. customThe organic phase was removed
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC chromatography (Method 21), which
  6. customgave 21 mg (33% yield, 96% pure) of the target compound

出典と根拠

ORDレコード
ord-668a8044e64543778e8a3071be19a694
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09422285B2

反応ノート

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