Potassium Carbonate → 1''-(5-Ethyl-pyrimidin-2-yl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406340ノート

反応式

HRID 2406340 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[CH2:27][C:18]4([CH2:26][C:20]5([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)[CH2:19]4)[O:17][C:14]3=[CH:15][N:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl[C:29]1[N:34]=[CH:33][C:32]([CH2:35][CH3:36])=[CH:31][N:30]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>O>[CH2:35]([C:32]1[CH:31]=[N:30][C:29]([N:23]2[CH2:22][CH2:21][C:20]3([CH2:26][C:18]4([O:17][C:14]5=[CH:15][N:16]=[C:11]([C:8]6[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=6)[CH:12]=[C:13]5[CH2:27]4)[CH2:19]3)[CH2:25][CH2:24]2)=[N:34][CH:33]=1)[CH3:36]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 35727632-Chloro-5-ethylpyrimidineHCID 867012015-(4-Methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

生成物 1

HCID 721948521''-(5-Ethyl-pyrimidin-2-yl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of 5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (HCl salt; 50 mg), 2-chloro-5-ethyl-pyrimidine (18 mg), potassium carbonate (35 mg), and N-methyl-pyrrolidinone (2 ml) is stirred at 80° C. for 4 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→1:9) to give the title compound. LC (method 1): tR=1.16 min; Mass spectrum (ESI+): m/z=491 [M+H]+.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe resulting mixture is extracted with ethyl acetate
  3. dry with materialThe combined extracts are dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→1:9)

出典と根拠

ORDレコード
ord-eb59890ad9d44ef1aa5f46a5345576a3
出典データセット
uspto-grants-2014_08
特許番号
US08809361B2

反応ノート

読み込み中…