Hydrochloric Acid → [(11S)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]methanol

HRID 221577노트

반응식

HRID 221577 반응식
C([O:8][CH2:9][C@@H:10]1[N:15]2[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[C:18]([NH2:26])[C:17]=3[N:27]=[C:14]2[CH2:13][O:12][CH2:11]1)C1C=CC=CC=1.Cl>CO.[Pd].C(O)C>[NH2:26][C:18]1[C:17]2[N:27]=[C:14]3[CH2:13][O:12][CH2:11][C@H:10]([CH2:9][OH:8])[N:15]3[C:16]=2[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1

참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 11639085(11S)-11-[(benzyloxy)methyl]-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

생성물 1

HCID 11623169[(11S)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]methanol수율 38.1%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

(11S)-11-[(Benzyloxy)methyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (297 mg, 0.825 mmol) was dissolved in 20 mL of methanol and the solution was placed in a pressure bottle. Palladium on carbon (10%, 230 mg) and 0.5 mL of 3 M HCl in ethanol were then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 18 hours, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with methanol and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in H2O and the solution was made basic by the addition of concentrated aqueous NH4OH solution. The aqueous solution was extracted with 10% MeOH/CH2Cl2 several times and the combined organic layers were concentrated under reduced pressure. Chromatography (SiO2, 25-75% CMA/CHCl3) gave a white powder. Crystallization from ethyl acetate gave 85 mg of the title compound as white, fluffy crystals, mp 238.6-239.8° C.

후처리

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with methanol
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in H2O
  6. additionthe solution was made basic by the addition of concentrated aqueous NH4OH solution
  7. extractionThe aqueous solution was extracted with 10% MeOH/CH2Cl2 several times
  8. concentrationthe combined organic layers were concentrated under reduced pressure
  9. customChromatography (SiO2, 25-75% CMA/CHCl3) gave a white powder
  10. customCrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-07df4c776ab04604a48244104cb25140
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207162B2

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