Trifluoroacetic acid → HCID 66575836, compound

HRID 2208698Notes

Reaction equation

HRID 2208698 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:24](=[O:36])[NH:25][CH2:26][C:27]2[C:28](=[O:35])[NH:29][C:30]([CH3:34])=[CH:31][C:32]=2[CH3:33])[C:5]([CH3:23])=[C:6]([N:8]([CH3:22])[CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH3:22])[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:5]([CH3:23])=[C:4]([CH:3]=1)[C:24]([NH:25][CH2:26][C:27]1[C:28](=[O:35])[NH:29][C:30]([CH3:34])=[CH:31][C:32]=1[CH3:33])=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86719537Tert-butyl 4-((5-chloro-3-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-2-methylphenyl)(methyl)amino)piperidine-1-carboxylate

Product 1

HCID 66575836HCID 66575836, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of tert-butyl 4-((5-chloro-3-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-2-methylphenyl)(methyl)amino)piperidine-1-carboxylate (0.2 g, 0.632 mmol) in DCM (5 mL) was cooled to 0° C. and TFA (0.15 mL) was added to it. Reaction mass was stirred at room temperature for 1 h. On completion, reaction was concentrated to dryness. Residue was purified by solvent washings to afford the desired compound (0.14 g, 53%) as its TFA salt. LCMS: 417.25 (M+1)+; HPLC: 96.16% (@ 254 nm) (Rt; 4.677; Method: Column: YMC ODS-A 150 mm×4.6 mm×5μ; Mobile Phase: A; 0.05% TFA in water/B; 0.05% TFA in acetonitrile; Inj. Vol: 10 μL, Col. Temp.: 30° C.; Flow rate: 1.4 mL/min.; Gradient: 5% B to 95% B in 8 min, Hold for 1.5 min, 9.51-12 min 5% B); 1H NMR (DMSO-d6, 400 MHz) δ 11.47 (s, 1H), 8.49 (bs, 1H), 8.20 (t, 1H), 8.18 (bs, 1H), 7.19 (s, 1H), 6.96 (s, 1H), 5.86 (s, 1H), 4.25 (d, 2H, J=4.4 Hz), 3.25 (d, 2H, J=12 Hz), 3.08 (m, 1H), 2.88 (bs, 2H), 2.56 (s, 3H), 2.18 (s, 3H), 2.17 (s, 3H), 2.10 (s, 3H), 1.76 (bs, 4H).

Workup

  1. customReaction mass
  2. customOn completion, reaction
  3. concentrationwas concentrated to dryness
  4. customResidue was purified by solvent washings

Sources & evidence

ORD record
ord-df59b00dc8d74db29aeeb09d01d592ce
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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