Phosphoric Acid → 4-cyclohexyl-1,7-diethyl-5-methyl-1,8-naphthyridin-2(1H)-one

HRID 398840

반응식

HRID 398840 반응식
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(=O)(O)(O)O.[NH2:20][C:21]1[N:26]([CH2:27][CH3:28])[C:25](=[O:29])[CH:24]=[C:23]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:22]=1.[CH3:36][C:37](=O)[CH2:38][C:39](=O)[CH2:40][CH3:41].[OH-].[Na+]>>[CH:30]1([C:23]2[C:22]3[C:21](=[N:20][C:39]([CH2:40][CH3:41])=[CH:38][C:37]=3[CH3:36])[N:26]([CH2:27][CH3:28])[C:25](=[O:29])[CH:24]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

참가 물질

6

반응물 5

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 763552,4-HexanedioneHCID 189692166-amino-4-cyclohexyl-1-ethyl-2(1H)-pyridone

생성물 1

HCID 189691894-cyclohexyl-1,7-diethyl-5-methyl-1,8-naphthyridin-2(1H)-one

반응 조건

온도
140 °C

실험 절차

A mixture of 5.0 g of diphosphorus pentoxide and 2.5 ml of phosphoric acid was stirred at 140° C. until it became transparent. Then, 1.1 g of 6-amino-4-cyclohexyl-1-ethyl-2(1H)-pyridone and 0.6 ml of 2,4-hexanedione were added to this solution, and the mixture was stirred at 140° C. for 3 hours. The reaction solution was poured into ice water, made alkaline by adding 1 N sodium hydroxide aqueous solution and then extracted with ethyl acetate. After drying the ethyl acetate layer over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (toluene-ethyl acetate) to give 1.2 g of 4-cyclohexyl-1,7-diethyl-5-methyl-1,8-naphthyridin-2(1H)-one.

후처리

  1. stirringthe mixture was stirred at 140° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialAfter drying the ethyl acetate layer over anhydrous magnesium sulfate, magnesium sulfate
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was then purified by silica gel column chromatography (toluene-ethyl acetate)

출처 및 근거

ORD 기록
ord-416e61b81e344a528749ac9bcb03a80d
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817670

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