Sodium Bicarbonate → [1-[2-[(Methylsulphonyl)amino]ethyl]-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate

HRID 53246노트

반응식

HRID 53246 반응식
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14](Cl)=O)[O:4][N:3]=1.OC[CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:21][CH2:20]1.[C:32](=[O:35])(O)[O-:33].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH3:31][S:28]([NH:27][CH2:26][CH2:25][N:22]1[CH2:21][CH2:20][CH:19]([O:33][C:32](=[O:35])[N:13]([CH3:14])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:5]2[O:4][N:3]=[C:2]([CH3:1])[N:6]=2)[CH2:24][CH2:23]1)(=[O:29])=[O:30]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 19962114N-(2-(4-(hydroxymethyl)piperidin-1-yl)ethyl)methanesulfonamideHCID 19962135[2-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamoyl Chloride

생성물 1

HCID 70079874[1-[2-[(Methylsulphonyl)amino]ethyl]-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate

시약·촉매·용매 1

HCID 21863594Toluene ethanol용매

실험 절차

[2-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamoyl chloride (7.5 g) was placed in a flask equipped with an air stirrer and ground to a powder N-[2-[4-(Hydroxymethyl)-1-piperidinyl]ethyl]methanesulphonamide (9.33 g) was added and the solids intimately mixed under nitrogen for 10 min at room temperature. The mixture was stirred under a stream of nitrogen at 150° for 10 min. The mixture was allowed to cool then toluene/ethanol (10:1; 110 ml) was cautiously added followed by 8% sodium bicarbonate solution. The mixture was vigorously stirred, the layers were separated and the aqueous phase extracted with 10% ethanol in dichloromethane (4×100 ml). The organic solutions were combined and dried and concentrated in vacuo to give a beige solid. This was purified by FCC eluting with System A (100:8:1) to give the title compound (11.83 g) as fluffy off-white needles.

후처리

  1. customequipped with an air stirrer
  2. additionthe solids intimately mixed under nitrogen for 10 min at room temperature
  3. temperatureto cool
  4. stirringThe mixture was vigorously stirred
  5. customthe layers were separated
  6. extractionthe aqueous phase extracted with 10% ethanol in dichloromethane (4×100 ml)
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto give a beige solid
  10. customThis was purified by FCC
  11. washeluting with System A (100:8:1)

출처 및 근거

ORD 기록
ord-6d73ce3c728e48c89310726c630ef4b7
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618827

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