Cesium carbonate → Benzyl 4-{[(5-fluoro-pyrimidin-2-yl)amino]methyl}piperidine-1-carboxylate

HRID 1351591ノート

反応式

HRID 1351591 の反応式
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1.Cl[C:20]1[N:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[F:26][C:23]1[CH:22]=[N:21][C:20]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:10])[CH2:5][CH2:4]2)=[N:25][CH:24]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 5834662-Chloro-5-fluoropyrimidineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

生成物 1

HCID 10132254Benzyl 4-{[(5-fluoro-pyrimidin-2-yl)amino]methyl}piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A stirred mixture of benzyl 4-(aminomethyl)-piperidine-1-carboxylate (EXAMPLE 13, STEP 1) (10.0 g, 0.040 mol), 2-chloro-5-fluoropyrimidine (5.3 g, 0.040 mol) and cesium carbonate (26.2 g, 0.081 mol) in DMF (100 mL) was heated at 100° C. for 2 h. The reaction mixture was cooled to rt, diluted with ethyl acetate (400 mL), washed with aqueous saturated NaHCO3 (100 mL), water (5×100 mL), and brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel 60 (0.5 kg), eluting with 50–100% ethyl acetate in hexane to give the title compound. M.S. (M+1): 345.

後処理

  1. temperatureThe reaction mixture was cooled to rt
  2. washwashed with aqueous saturated NaHCO3 (100 mL), water (5×100 mL), and brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel 60 (0.5 kg)
  7. washeluting with 50–100% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-8499a8e2e7084af1bcf8e56c9928737b
出典データセット
uspto-grants-2007_05
特許番号
US07217716B2

反応ノート

読み込み中…