Morpholine → 6,6-Dimethyl-8-(1-oxetan-3-yl-piperidin-4-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2202436노트

반응식

HRID 2202436 반응식
[NH:1]1[CH2:6][CH2:5]O[CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:21]([C:23]1[CH:24]=[CH:25][C:26]2[C:38](=[O:39])[C:37]3[C:36]4[C:31](=[CH:32][C:33]([C:40]#[N:41])=[CH:34][CH:35]=4)[NH:30][C:29]=3[C:28]([CH3:43])([CH3:42])[C:27]=2[CH:44]=1)=O.[O:45]1[CH2:48][C:47](=O)[CH2:46]1>C1COCC1>[CH3:42][C:28]1([CH3:43])[C:29]2[NH:30][C:31]3[C:36](=[CH:35][CH:34]=[C:33]([C:40]#[N:41])[CH:32]=3)[C:37]=2[C:38](=[O:39])[C:26]2[CH:25]=[CH:24][C:23]([CH:21]3[CH2:3][CH2:2][N:1]([CH:47]4[CH2:46][O:45][CH2:48]4)[CH2:6][CH2:5]3)=[CH:44][C:27]1=2

참가 물질

6

반응물 4

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 866638188-Formyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

생성물 1

HCID 533573286,6-Dimethyl-8-(1-oxetan-3-yl-piperidin-4-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

With the same condition as the method for synthesizing the Compound B3-32 (morpholine (6 μl, 1.5 eq.) and sodium triacetoxy borohydride (81 mg, 2.0 eq.) were added to THF (1 ml) solution of the Compound B2-29: 8-formyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (30 mg, 0.095 mmol), and stirred at room temperature for 1 hour. The reaction solution was filtered to remove insoluble matters. The residues obtained after concentration under reduced pressure were purified by high performance liquid chromatography to obtain the Compound B3-32 (6,6-dimethyl-8-morpholin-4-yl methyl-11-oxo-6,11-dihydro-5H-benzo carbazole-3-carbonitrile) (19 mg, 50%)), the title compound was synthesized from the Compound B3-13-2 and oxetan-3-one.

후처리

  1. customWith the same condition as the method for synthesizing the Compound
  2. filtrationThe reaction solution was filtered
  3. customto remove insoluble matters
  4. customThe residues obtained
  5. concentrationafter concentration under reduced pressure
  6. customwere purified by high performance liquid chromatography
  7. customto obtain the Compound

출처 및 근거

ORD 기록
ord-1952870e6d774c6aa6359839fe36fe86
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365514B2

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