Hydrochloric Acid → HCID 22137314, compound

HRID 1827548Notes

Reaction equation

HRID 1827548 reaction equation
[Cl:1][C:2]1[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[C:3]=1[C:4]([N:6]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:23][CH:22]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C2CCCCO2)[CH:9]=1)=[O:5].Cl.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>CO.O1CCOCC1>[Cl:1][C:2]1[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[C:3]=1[C:4]([N:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1)[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:25][CH:26]=1)=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 22137343HCID 22137343, compound

Product 1

HCID 22137314HCID 22137314, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of crude 2,4,6-trichloro-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzamide (0.076 g, 0.13 mmol) prepared in Step A in 0.5 mL methanol was added HCl (0.78 mL of a 4.0M solution in 1,4-dioxane, 3.12 mmol) and triethylsilane (0.20 mL, 1.30 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. The residue was purified by preparative TLC (1.0 mm silica gel layer, eluting with 10% methanol/methylene chloride) to afford 0.022 g of 2,4,6-trichloro-N-(3-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzamide. 1H NMR (CDCl3) δ 7.13 (s, 2H), 7.10–7.05 (m, 1H), 7.03 (d, 2H, J=12.0 Hz), 6.79–6.67 (m, 3H), 6.58 (d, 2H, J=11.6 Hz), 4.94 (s, 2H), 4.17–4.13 (m, 2H), 3.15 (bs, 2H), 2.99 (bs, 4H), 1.94 (bs, 4H).

Workup

  1. washthe aqueous solution was washed with methylene chloride
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC (1.0 mm silica gel layer, eluting with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-df3f76f3a9b84f29a97f0a3f77b0b37a
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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