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

HRID 1943670ノート

反応式

HRID 1943670 の反応式
[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

参加物

8

反応物 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

生成物 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)-methanone収率 231.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-3f85de2900224204a8f0a4993c156fee
出典データセット
uspto-grants-2013_03
特許番号
US08394792B2

反応ノート

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