Water → HCID 178461553、化合物

HRID 522812ノート

反応式

HRID 522812 の反応式
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7](C3C=CC=C4C=3C=CN4)[NH:8]2)=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][C@H:21]2C)[N:3]=1.[O:27]1[CH2:33][CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[CH3:34]CN(C(C)C)C(C)C.O>C(O)CCC>[CH3:34][C@@H:28]1[O:27][C@H:33]([CH3:32])[CH2:31][N:30]([C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][NH:8]3)=[C:4]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[N:3]=2)[CH2:29]1

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 218732751,4-OxazepaneHCID 178461591HCID 178461591、化合物

生成物 1

HCID 178461553HCID 178461553、化合物収率 78.5%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
120 °C

実験手順

To the solution of 2-chloro-8-(1H-indol-4-yl)-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (50 mg, 0.14 mmol) in 1-butanol (300 μL) was added 1,4-oxazepane (20.6 mg, 0.20 mmol), followed by DIPEA (47.4 μL, 0.27 mmol). The mixture was stirred at 120° C. for 24 hours. Upon completion of the reaction, the solution was poured into water. The aqueous layer was extracted with CH2Cl2 three times. The combined organic layers were dried over Na2SO4, filtered, concentrated under reduced pressure and the crude was purified by flash column chromatography (30-100% EtOAc/cyclohexane gradient) to provide 2-((2S,6R)-2,6-dimethyl-morpholin-4-yl)-6-morpholin-4-yl-9H-purine (35 mg, 59%) as a beige solid. LC-MS at 254 nm; [M+H] 432.3; Rt 1.00 min; (LCMS method 1).

後処理

  1. customUpon completion of the reaction
  2. extractionThe aqueous layer was extracted with CH2Cl2 three times
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customthe crude was purified by flash column chromatography (30-100% EtOAc/cyclohexane gradient)

出典と根拠

ORDレコード
ord-37f2b30fc4ee4019a1389f24dd1dcbfa
出典データセット
uspto-grants-2016_05
特許番号
US09334271B2

反応ノート

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