Hydrochloric Acid → (2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

HRID 1943670노트

반응식

HRID 1943670 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[CH:19]=[CH:20][N:21]=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([F:10])[C:7]=1[O:8]C.[Br-].[Li+].N1CCNCC1.Cl>O.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[CH:19]=[CH:20][N:21]=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([F:10])[C:7]=1[OH:8].[O:16]1[CH2:17][CH2:18][N:13]([CH:11]=[O:12])[C:14]2[CH:22]=[N:21][CH:20]=[CH:19][C:15]1=2

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 82050Lithium BromideHCID 44608224(3,5-Difluoro-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

생성물 2

HCID 44608225(3,5-Difluoro-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanoneHCID 86650558(2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone수율 231.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

In a 10 ml flask, (3,5-difluoro-4-methoxy-phenyl)-(2,3-dihydro -pyrido[4,3-b][1,4]oxazin-4-yl)-methanone (50 g, 0.163 mmol), lithium bromide (57 mg, 0.65 mmol) and piperazine (21 mg, 0.24 mmol) were dissolved with N,N-dimethyl formamide, and stirred at 1000 for 3 hours. After completion of the reaction by adding water dropwise, the mixture was adjusted to weak acidic condition (pH=6) by using 1N hydrochloric acid, and the formed solid was filtered and washed with distilled water and ethyl acetate. The resulting solid was recrystallized from methanol to obtain the target compound 29, i.e., 3,5-difluoro-4-hydroxy -phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone (31 mg, 65%).

후처리

  1. customAfter completion of the reaction
  2. filtrationthe formed solid was filtered
  3. washwashed with distilled water and ethyl acetate
  4. customThe resulting solid was recrystallized from methanol

출처 및 근거

ORD 기록
ord-3f85de2900224204a8f0a4993c156fee
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394792B2

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