Acetic Acid → Laniquidar

HRID 1016375

反応式

HRID 1016375 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][C:24](=[C:27]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[CH2:31][CH2:30][N:29]4[C:38]([CH:41]=[O:42])=[CH:39][N:40]=[C:28]34)[CH2:23][CH2:22]2)=[CH:15][CH:14]=1.[O-:43][C:44]#N.[Na+].C(O)(=O)C>CO.[O-2].[O-2].[Mn+4]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][C:24](=[C:27]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[CH2:31][CH2:30][N:29]4[C:38]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][N:40]=[C:28]34)[CH2:25][CH2:26]2)=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 517096Sodium CyanateHCID 99156646,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-carboxaldehyde

生成物 1

HCID 6450806Laniquidar収率 87.9%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 887Methanol溶媒

実験手順

A mixture of compound 4 (164 g), sodium cyanate (80 g) and manganese dioxide (500 g) in methanol (5.5 l) was stirred at room temperature. Ethanoic acid (122 g) was added dropwise and the resulting reaction mixture was stirred and refluxed overnight. The reaction mixture was filtered over dicalite, and the filter residue was rinsed with CH3OH/CH2Cl2. The filtrate was evaporated. The residue was partitioned between DCM and aqueous K2CO3 solution. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from ACN. The precipitate was filtered off and dried, yielding 152 g (87%) of methyl 6,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]-benzazepine-3-carboxylate (compound 6, mp. 179.3° C.).

後処理

  1. customthe resulting reaction mixture
  2. stirringwas stirred
  3. temperaturerefluxed overnight
  4. filtrationThe reaction mixture was filtered over dicalite
  5. washthe filter residue was rinsed with CH3OH/CH2Cl2
  6. customThe filtrate was evaporated
  7. customThe residue was partitioned between DCM and aqueous K2CO3 solution
  8. customThe organic layer was separated
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from ACN
  13. filtrationThe precipitate was filtered off
  14. customdried

出典と根拠

ORDレコード
ord-1a2647c23b4245aaa0854e2afacd6b86
出典データセット
uspto-grants-2002_11
特許番号
US06476018B1

関連ノート

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