N,N'-Dimethylethylenediamine → 2-{4-[(1R,2R)-2-({[4-(cyclopropylsulfonyl)benzyl]oxy}methyl)cyclopropyl]piperidin-1-yl}-5-ethylpyrimidine

HRID 1468841노트

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HRID 1468841 반응식
Br[C:2]1[CH:27]=[CH:26][C:5]([CH2:6][O:7][CH2:8][C@@H:9]2[CH2:11][C@@H:10]2[CH:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH:28]1([S:31]([O-:33])=[O:32])[CH2:30][CH2:29]1.[Na+].CNCCNC>CS(C)=O>[CH:28]1([S:31]([C:2]2[CH:27]=[CH:26][C:5]([CH2:6][O:7][CH2:8][C@@H:9]3[CH2:11][C@@H:10]3[CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[N:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][N:19]=4)[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)(=[O:33])=[O:32])[CH2:30][CH2:29]1

참가 물질

5

반응물 3

HCID 8070N,N'-DimethylethylenediamineHCID 42643363Sodium cyclopropanesulfinateHCID 711352722-[4-((1R,2R)-2-{[(4-bromobenzyl)oxy]methyl}cyclopropyl)piperidin-1-yl]-5-ethyl pyrimidine

생성물 1

HCID 867177912-{4-[(1R,2R)-2-({[4-(cyclopropylsulfonyl)benzyl]oxy}methyl)cyclopropyl]piperidin-1-yl}-5-ethylpyrimidine

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
120 °C

실험 절차

The product of example 54 (step A) (100 mg, 0.2 mmol), sodium cyclopropanesulfinate (36 mg, 0.28 mmol), copper (I) trifluoromethanesulfonate benzene complex (6 mg, 0.012 mmol), and N,N′-dimethylethylenediamine (2 mg, 0.02 mmol) were dissolved in DMSO (1 mL), and the solution was heated at 120° C. The solution was partitioned between water and Et2O. The aqueous layer was extracted with Et2O. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified via silica gel column chromatography (2/1 EtOAc/hexanes) to provide the title compound. MS (ESI) m/z 456 [M+H]+. GPR119 Human EC50: 1.2 nM

후처리

  1. customThe solution was partitioned between water and Et2O
  2. extractionThe aqueous layer was extracted with Et2O
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via silica gel column chromatography (2/1 EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-95f3e728e20540ef9b914e06b1247593
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006228B2

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