Water → HCID 178461553, 화합물

HRID 522812노트

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HRID 522812 반응식
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

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 218732751,4-OxazepaneHCID 178461591HCID 178461591, 화합물

생성물 1

HCID 178461553HCID 178461553, 화합물수율 78.5%

시약·촉매·용매 1

HCID 2631-Butanol용매

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온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-37f2b30fc4ee4019a1389f24dd1dcbfa
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334271B2

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