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

HRID 2275096Notes

Reaction equation

HRID 2275096 reaction equation
Cl.[CH3:2][C:3]1([CH3:31])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[N:17])[CH:12]=3)[C:7]=2[C:6](=[O:18])[C:5]2[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:22][C:4]1=2.[O:32]1[CH2:35][C:34](=O)[CH2:33]1.C1COCC1.C([BH3-])#N.[Na+]>C(O)(=O)C.O.CO>[CH3:2][C:3]1([CH3:31])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[N:17])[CH:12]=3)[C:7]=2[C:6](=[O:18])[C:5]2[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([CH:34]4[CH2:35][O:32][CH2:33]4)[CH2:27][CH2:26]3)=[CH:22][C:4]1=2

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 668343006,6-Dimethyl-11-oxo-8-(piperidin-4-ylmethoxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloric acid salt

Product 1

HCID 668344386,6-Dimethyl-8-(1-oxetan-3-yl-piperidin-4-ylmethoxy)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 43.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6,6-Dimethyl-11-oxo-8-(piperidin-4-ylmethoxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloric acid salt (Compound A7-25, 30 mg, 0.075 mmol) and oxetan-3-one (38 mg, 7 eq.) were dissolved in acetic acid (0.2 ml), THF (1 ml) and methanol (1 ml), added with sodium cyanoborohydride (33 mg, 7 eq.) at room temperature, and stirred overnight. The reaction solution was added with water, and then extracted with ethyl acetate. The solution was dried over sodium sulfate and the solvent was removed under vacuum and the resulting residues were purified by preparative TLC (chloroform:2 N ammonia methanol=9:1) to obtain the target compound (15 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe solution was dried over sodium sulfate
  3. customthe solvent was removed under vacuum
  4. customthe resulting residues were purified by preparative TLC (chloroform:2 N ammonia methanol=9:1)

Sources & evidence

ORD record
ord-f5be6e1fcbac4b57bacef100f42c9914
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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