HCID 22034100, compound → HCID 22034139, compound

HRID 1792286Notes

Reaction equation

HRID 1792286 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([NH:14][CH2:15][CH2:16][NH:17][C:18]2[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([O:25][C:26]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=3[CH3:34])[C:19]=2[CH3:35])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>C1COCC1.CO.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:14][CH2:15][CH2:16][NH:17][C:18]2[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([O:25][C:26]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=3[CH3:34])[C:19]=2[CH3:35])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 1

HCID 22034100HCID 22034100, compound

Product 1

HCID 22034139HCID 22034139, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add BH3 in THF (1 M solution, 0.3 mmol, 0.3 mL) to a solution of the crude 2-(3,4-dimethoxyphenyl)-N-(2-{[3,6-dimethyl-2-(2,4,6-trimethylphenoxy)(4-pyridyl)]amino}ethyl) acetamide in THF (2.0 mL) at ambient temperature. Heat the reaction mixture under reflux for 15 h, dilute with a solution of 10% aq HCV/MeOH (1:1, 2 mL) and heat again under reflux (1 h). Dilute the reaction mixture with CHCl3 (10 mL), wash with saturated aq NaHCO3 (1×5 mL), dry and concentrate in vacuo. Chromatograph the crude residue on SiO2-gel using a gradient of 100% EtOAc to 10% Et2NH/EtOAc to obtain the title compound as a colorless oil. Immediately dissolve the product in Et2O (1 mL), treat with excess 4 M HCl/dioxane and concentrate in vacuo to obtain the hydrochloride salt of the title compound as a colorless solid. 1H NMR (d4-MeOH, Unity 400): d 6.99–6.77 (6H, m), 3.81 (3H, s), 3.78 (3H, s), 3.62 (2H, m), 2.98 (2H, t), 2.39 (3H, s), 2.29 (3H, s), 2.16 (3H, s), 2.07 (6H, s). M+1: 464.

Workup

  1. temperatureHeat the reaction mixture
  2. temperatureunder reflux for 15 h
  3. temperatureheat again
  4. temperatureunder reflux (1 h)
  5. washwash with saturated aq NaHCO3 (1×5 mL)
  6. customdry
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6f046879ca3246f4b57f746bea94b86f
Source dataset
uspto-grants-2006_07
Patent number
US07074929B2

Reaction notes

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