Trifluoroacetic acid → HCID 59743883, compound

HRID 602085Notes

Reaction equation

HRID 602085 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:13]([NH:14][C:15]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=4)=[CH:21][CH:22]=3)=[O:16])[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[F:29][C:25]1[CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][C:17]([C:15]([NH:14][CH:13]3[CH2:12][CH2:11][NH:10][CH2:9][CH:8]3[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:16])=[CH:18][N:19]=2)[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67266971HCID 67266971, compound

Product 1

HCID 59743883HCID 59743883, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-fluorophenyl)-4-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)piperidine-1-carboxylate (348 mg, 0.71 mmol) in CH2Cl2 (5 mL) at 0° C. was added TFA (1.2 mL). After stirring overnight at rt the the reaction was diluted with toluene (5 mL) and then the solvent removed and the residue purified by chromatography (silica, 10% MeOH/DCM) to give the desired product, 6-(3-fluorophenyl)-N-[3-(4-fluorophenyl)piperidin-4-yl]nicotinamide. (168 mg, 61% yield). 1H NMR (400 MHz, DMSO-d6) □ ppm 8.87 (1H, d, J=2.0 Hz), 8.52 (1H, s), 8.04-8.15 (2H, m), 8.00 (2H, d, J=7.9 Hz), 7.58 (1H, d, J=6.1 Hz), 7.35 (4H, dd, J=9.0, 3.5 Hz), 7.08-7.22 (2H, m), 4.60-4.72 (1H, m), 3.81 (1H, t), 3.05-3.27 (4H, m), 1.91 (1H, s). LC/MS=(M+H)=394.1 observed, 394.17 expected.

Workup

  1. customthe solvent removed
  2. customthe residue purified by chromatography (silica, 10% MeOH/DCM)

Sources & evidence

ORD record
ord-e13dcbc07f594065b1b89b5cffb852d4
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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