Acetic Acid → HCID 70874148, compound

HRID 2208716Notes

Reaction equation

HRID 2208716 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:22]([CH3:29])[CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8].[C:30](O)(=[O:32])[CH3:31].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CS(C)=O>[C:30]([N:26]1[CH2:27][CH2:28][CH:23]([N:22]([CH3:29])[C:4]2[C:5]([CH3:21])=[C:6]([CH:20]=[C:2]([Br:1])[CH:3]=2)[C:7]([NH:9][CH2:10][C:11]2[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=2[CH3:17])=[O:8])[CH2:24][CH2:25]1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724699PyBOPHCID 66575763HCID 66575763, compound

Product 1

HCID 70874148HCID 70874148, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-3-(methyl(piperidine-4-yl)amino)benzamide (0.2 g, 0.447 mmol) dissolved in DMSO (2 mL) and acetic acid (0.054 g, 0.896 mmol) were added to it. The reaction mixture was stirred at room temperature for 15 min before PYBOP (0.342 g, 0.672 mmol) was added to it and stirring was continued for overnight. After completion, reaction mass was poured into ice, and extracted using 10% MeOH/DCM. Combined organic layers were dried, concentrated to provide crude material, which then purified with column chromatography using silica (100-200 mesh size) to afford the desired compound (0.15 g, 17%). LCMS: 503.20 (M+1)+; HPLC: 96.06% (@ 254 nm) (Rt; 5.143; 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 11.48 (s, 1H), 8.21 (t, 1H, J=4.8 Hz), 7.23 (d, 1H, J=1.6 Hz), 7.04 (d, 1H, J=1.6 Hz), 5.85 (s, 1H), 4.32 (d, 1H, J=12.4 Hz), 4.23 (d, 2H, J=4.8 Hz), 3.77 (d, 1H, J=13.2 Hz), 2.98 (t, 2H, J=11.2 Hz), 2.54 (s, 3H), 2.18 (s, 3H), 2.13 (s, 3H), 2.10 (s, 3H), 1.97 (s, 3H), 1.53-1.60 (m, 4H), 1.38-1.41 (m, 1H).

Workup

  1. additionwas added to it
  2. customAfter completion, reaction mass
  3. additionwas poured into ice
  4. extractionextracted
  5. customCombined organic layers were dried
  6. concentrationconcentrated
  7. customto provide crude material, which
  8. customthen purified with column chromatography

Sources & evidence

ORD record
ord-bfbf4d17b99643a286f34502800aebaa
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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