Trifluoroacetic acid → 6,6-Dimethyl-11-oxo-8-(piperidin-4-yloxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61716Notes

Reaction equation

HRID 61716 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:23]=[CH:24][C:25]3[C:37](=[O:38])[C:36]4[C:35]5[C:30](=[CH:31][C:32]([C:39]#[N:40])=[CH:33][CH:34]=5)[NH:29][C:28]=4[C:27]([CH3:42])([CH3:41])[C:26]=3[CH:43]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C1COCC1>[CH3:41][C:27]1([CH3:42])[C:28]2[NH:29][C:30]3[C:35](=[CH:34][CH:33]=[C:32]([C:39]#[N:40])[CH:31]=3)[C:36]=2[C:37](=[O:38])[C:25]2[CH:24]=[CH:23][C:22]([O:21][CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[CH:43][C:26]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 668342114-(3-Cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 668342296,6-Dimethyl-11-oxo-8-(piperidin-4-yloxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 133.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

THF (0.5 mL) and TFA (0.5 mL) were added to 4-(3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (Compound A7-1, 35 mg, 0.072 mmol), and the mixture was stirred at room temperature until Compound A7-1 disappears. The reaction solution was concentrated under reduced pressure and the residue was desalinated by using anion exchanger PL StratoSpheres (trademark) PL-HCO3 MP to obtain the title compound (37 mg, 76%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e0996ab7ce44324b6447b7925d1afce
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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