Trifluoroacetic acid → 4-[2,6-Bis-(4-cyanophenoxy)pyridine-3-carbonyl]piperazine

HRID 1024686Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=3)=[N:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:38]([C:35]1[CH:36]=[CH:37][C:32]([O:31][C:17]2[C:16]([C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[O:15])=[CH:21][CH:20]=[C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[N:18]=2)=[CH:33][CH:34]=1)#[N:39]

Participants

Conditions

Temperature: 5 °C

Procedure

4-[2,6-Bis-(4-cyano-phenoxy)pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester 1.2 g (2.28 mmol) was dissolved in 5 ml of DCM at 5° C. under inert atmosphere. 0.7 ml of TFA was added over a 10 min period, while the temperature was maintained at 5° C. Stirring was continued for 1 h at RT and reaction progress was monitored by TLC. The reaction mixture was concentrated under reduced pressure and the residual crude product was purified by column chromatography using chloroform: ethylacetate (8:2) as eluant to afford 0.9 g of the required product. Percentage purity (LCMS): 88.2%, (M+1): 425.1. 1H NMR (DMSO-d6): δ 3.15 (2H, m), 3.22 (2H, m), 3.64 (2H, m), 3.85 (2H, m), 7.00 (1H, d), 7.34 (4H, t), 7.82 (4H, t), 8.08 (1H, d), 9.02 (1H, brs).

Workup

customreaction progress
concentrationThe reaction mixture was concentrated under reduced pressure
customthe residual crude product was purified by column chromatography

Sources & evidence

ORD record: ord-950e9ea3ceb6468cb81ef96f52f9a967
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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