Potassium Carbonate → 9-(Benzo[d]oxazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41556

반응식

HRID 41556 반응식
Cl.[C:2]1(=[O:13])[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].Cl[C:21]1[O:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1>CN(C=O)C>[O:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[N:10]1[CH2:11][CH2:12][C:7]2([C:2](=[O:13])[NH:3][CH2:4][CH2:5][CH2:6]2)[CH2:8][CH2:9]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 119862-ChlorobenzoxazoleHCID 450742882,9-Diazaspiro(5.5)undecan-1-one hydrochloride

생성물 1

HCID 672537129-(Benzo[d]oxazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To the stirred solution of 2,9-diazaspiro[5.5]undecan-1-one hydrochloride [1187173-73-4] (100 mg, 0.49 mmol) in DMF (3 mL) was added K2CO3 (203 mg, 1.47 mmol) and 2-chloro benzoxazole [615-18-9] (82.8 mg, 0.54 mmol). The mixture was heated at 60° C. for 18 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. To the crude mixture water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to obtain a yellow solid which was washed with diethyl ether and n-pentane to yield the title compound as solid (100 mg, 72%). [LCMS RtF=0.36 min, [M+H]+=286.1]

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. additionTo the crude mixture water was added
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain a yellow solid which
  9. washwas washed with diethyl ether and n-pentane

출처 및 근거

ORD 기록
ord-7d8c0276c0d2440aabcc1643f268cfba
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530648B2

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