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

HRID 1468841ノート

反応式

HRID 1468841 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-95f3e728e20540ef9b914e06b1247593
出典データセット
uspto-grants-2015_04
特許番号
US09006228B2

反応ノート

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