Toluene → 5-hydroxymethyl-4-{[(6-chloropyridin-3-yl)methyl]amino}furan-2(5H)-one

HRID 552916ノート

反応式

HRID 552916 の反応式
O[C:2]1[CH:6]([CH2:7][OH:8])[O:5][C:4](=[O:9])[CH:3]=1.[NH2:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1.C1(C)C=CC=CC=1.CN(C)C=O>C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(O)(=O)C>[OH:8][CH2:7][CH:6]1[O:5][C:4](=[O:9])[CH:3]=[C:2]1[NH:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 671646764-hydroxy-5-hydroxymethylfuran-2(5H)-one

生成物 1

HCID 866324475-hydroxymethyl-4-{[(6-chloropyridin-3-yl)methyl]amino}furan-2(5H)-one収率 22.3%

試薬・触媒・溶媒 3

HCID 6101p-Toluenesulfonic acid触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

905.0 mg (6.95 mmol) of 4-hydroxy-5-hydroxymethylfuran-2(5H)-one (VII-1a) and 991.8 mg (6.95 mmol) of 3-aminomethyl-6-chloropyridine are stirred in the mixture of 100.5 ml of toluene and 10 ml of N,N-dimethylformamide (DMF), and 10 mg of para-toluenesulphonic acid and 0.5 ml of acetic acid are added. With stirring, the entire reaction mixture is then heated at reflux on a water separator for about 18 hours. Concentration under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm; mobile phase: cyclohexane/acetone=1:1) gives 394.2 mg (22.2% of theory) of 5-hydroxymethyl-4-{[(6-chloropyridin-3-yl)methyl]amino}furan-2(5H)-one.

後処理

  1. additionare added
  2. customthe entire reaction mixture
  3. temperatureis then heated
  4. concentrationConcentration
  5. customunder reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm; mobile phase: cyclohexane/acetone=1:1)

出典と根拠

ORDレコード
ord-5e307ffabb1347589046470e52f20a7c
出典データセット
uspto-grants-2011_05
特許番号
US07951951B2

反応ノート

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