Hydrochloric Acid → HCID 11721163, compound

HRID 551903Notes

Reaction equation

HRID 551903 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:44]=[CH:43][C:16]([CH2:17][N:18]([CH2:32][C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35][CH:34]=3)[C:19]3[CH:31]=[CH:30][C:22]4[O:23]C(C)(C)[O:25][C:26](=[O:27])[C:21]=4[CH:20]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].O[Li].O.[ClH:48].[Na+].[Cl-]>O1CCOCC1.O>[ClH:48].[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:44]=[CH:43][C:16]([CH2:17][N:18]([CH2:32][C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35][CH:34]=3)[C:19]3[CH:31]=[CH:30][C:22]([OH:23])=[C:21]([CH:20]=3)[C:26]([OH:27])=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 11585057HCID 11585057, compound

Product 1

HCID 11721163HCID 11721163, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 6-[{4-[(4-butylphenyl)ethynyl]benzyl}(1-naphthylmethyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (72 mg, 0.12 mmol) in dioxane (2 ml) was added a solution of LiOH hydrate (25 mg, 0.60 mmol) in water (0.2 mL). The reaction mixture was heated at 80° C. for 2 hrs. Then a solution of HCl in dioxane (1 mL, 4N) and a saturated aqueous solution of NaCl (5 mL) were added and extracted with Et2O (2×10 mL). The combined organic layers were dried over Na2SO4 and the solvents were removed under reduced pressure. The residue was dissolved in a solution of HCl in Et2O (1 mL, 1N) and DCM (1 mL). Evaporation of the solvent under reduced pressure gave 41 mg (51%) of the title compound as a beige foam. HPLC, Rt: 5.8 min (purity: 82.7%). LC/MS, M+(ESI): 540.3, M−(ESI): 538.3. 1H NMR (CD3OD) δ: 7.97 (m, 3H), 7.72 (m, 1H), 7.58-7.41 (m, 11H), 7.23 (d, J=8.3 Hz, 2H), 6.92 (d, J=9.0 Hz, 1H), 5.42 (s, 2H), 5.11 (s, 2H), 2.67 (t, J=7.5 Hz, 2H), 1.64 (m, 2H), 1.38 (m, 2H), 0.98 (t, J=7.4 Hz, 3H).

Workup

  1. extractionextracted with Et2O (2×10 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvents were removed under reduced pressure
  4. dissolutionThe residue was dissolved in a solution of HCl in Et2O (1 mL, 1N) and DCM (1 mL)
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-66cc1484a3b24d9da9a0a743244af43d
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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