Water → 2-(3-chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylic acid N-(tetrahydropyran-4-ylmethyl)amide

HRID 38792

反応式

HRID 38792 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([C:19]([OH:21])=O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C([N:24]([CH2:27][CH3:28])CC)C.[O:29]1[CH2:34][CH2:33]C(CO)[CH2:31][CH2:30]1.O>C1(C)C=CC=CC=1>[O:29]1[CH2:34][CH2:33][CH:28]([CH2:27][NH:24][C:19]([C:12]2[C:13]([C:15]([F:18])([F:16])[F:17])=[N:14][C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:10][CH:11]=2)=[O:21])[CH2:31][CH2:30]1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 2773573(Oxan-4-yl)methanolHCID 167196552-(3-Chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylic acid

生成物 1

HCID 100704282-(3-chlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylic acid N-(tetrahydropyran-4-ylmethyl)amide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a mixture of 2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid (300 mg), triethylamine (197 μL), and toluene (6 mL) was added dropwise diphenyl phosphoric acid azide (265 μL), followed by stirring at room temperature for 30 minutes. Then, the mixture was stirred at 90° C. for 10 minutes, and a solution of tetrahydro-2H-pyran-4-yl methanol (131 mg) in toluene was added thereto, followed by heating with reflux for 2 hours. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate). The obtained pale yellow solid was washed with ethyl acetate-hexane to obtain tetrahydro-2H-pyran-4-ylmethyl {2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}carboxamide (178 mg) as a white solid.

後処理

  1. stirringThen, the mixture was stirred at 90° C. for 10 minutes
  2. temperatureby heating
  3. temperaturewith reflux for 2 hours
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)
  10. washThe obtained pale yellow solid was washed with ethyl acetate-hexane

出典と根拠

ORDレコード
ord-6dee91be0f03458e8c4a3c6e16d4d6a1
出典データセット
uspto-grants-2013_09
特許番号
US08524727B2

関連ノート

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