Sodium Hydroxide → (11R)-11-(chloromethyl)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 1663456노트

반응식

HRID 1663456 반응식
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[C:15]2[N:16]=[C:17]3[CH2:22][O:21][CH2:20][C@H:19]([CH2:23]O)[N:18]3[C:14]=2[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.[OH-].[Na+]>C(#N)C>[Cl:3][CH2:23][C@@H:19]1[N:18]2[C:14]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:7]=[C:6]([NH2:5])[C:15]=3[N:16]=[C:17]2[CH2:22][O:21][CH2:20]1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 11623169[(11S)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]methanol

생성물 1

HCID 58406156(11R)-11-(chloromethyl)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine수율 62.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

Thionyl chloride (1.5 mL, 20.7 mmol) was added neat to [(11S)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]methanol (280 mg, 1.03 mmol). The nearly homogeneous yellow reaction mixture was heated to 70° C. for 2 hours and turned dark red. The reaction mixture was cooled to ambient temperature and poured over ice. While maintaining the temperature at 0° C., the pH of the mixture was brought to 14 with 50% aqueous NaOH. The resulting white suspension was extracted with CHCl3. The layers were separated and the organic layer was dried over Na2SO4 and concentrated under reduced pressure to provide a tan foam. The tan foam was slurried with acetonitrile and filtered to give 185 mg of (11R)-11-(chloromethyl)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a white solid.

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. additionpoured over ice
  3. temperatureWhile maintaining the temperature at 0° C.
  4. extractionThe resulting white suspension was extracted with CHCl3
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto provide a tan foam
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-80b11b44c4a24bef93fd2f6aa601c9b0
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034938B2

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