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

HRID 552916노트

반응식

HRID 552916 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6101p-Toluenesulfonic acid촉매HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5e307ffabb1347589046470e52f20a7c
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951951B2

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