Trifluoroacetic acid → Trifluoroacetic acid

HRID 2208794Notes

Reaction equation

HRID 2208794 reaction equation
[CH2:1]([N:4]([C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([C:25](=[O:37])[NH:26][CH2:27][C:28]2[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=2[CH3:34])[C:19]=1[CH3:38])[CH:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl>[CH2:1]([N:4]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[C:18]1[C:19]([CH3:38])=[C:20]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[C:25]([NH:26][CH2:27][C:28]1[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=1[CH3:34])=[O:37])[CH:2]=[CH2:3].[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90151207HCID 90151207, compound

Product 2

HCID 6422Trifluoroacetic acidYield 37%HCID 89052983HCID 89052983, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of compound tert-butyl 4-(allyl (5-chloro-3-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-2-methylphenyl)amino)piperidine-1-carboxylate (0.2 g, 0.36 mmol) in DCM (5 mL) was cooled to 0° C. and TFA (0.5 mL) was added. The mixture was stirred at room temperature for 18 h. and concentrated to dryness. The residue was washed with diethyl ether and then purified by preparative HPLC to afford the title compound as TFA salt (0.06 g, 37%). LCMS: 443.25 (M+1)+; HPLC: 97.14% (@ 254 nm) (Rt; 5.074; 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 11.46 (s, 1H), 8.38 (bs, 1H), 8.21 (t, 1H), 8.05 (d, 1H), 7.21 (d, 1H, J=4.4 Hz), 6.97 (d, 1H, J=1.6 Hz), 5.86 (s, 1H), 5.56-5.64 (m, 1H), 4.97-5.09 (m, 2H), 4.24 (d, 2H, J=4.4 Hz), 3.62 (d, 2H, J=5.2 Hz), 3.23 (m, 2H), 3.10-3.16 (m, 1H), 2.85-2.88 (m, 2H), 2.19 (s, 3H), 2.18 (s, 3H), 2.10 (s, 3H), 1.83-1.86 (m, 2H), 1.68-1.73 (m, 2H).

Workup

  1. concentrationconcentrated to dryness
  2. washThe residue was washed with diethyl ether
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-510e9b4117fb48d1a7caaa2e8a89b89b
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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