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

HRID 2202436Notes

Reaction equation

HRID 2202436 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1952870e6d774c6aa6359839fe36fe86
Source dataset
uspto-grants-2016_06
Patent number
US09365514B2

Reaction notes

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