Hydrochloric Acid → HCID 69591910, compound

HRID 1827582Notes

Reaction equation

HRID 1827582 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH:9][C:10](=[O:46])[CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([O:39]C4CCCCO4)[CH:34]=3)[S:20]([C:23]3[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=3[CH3:31])(=[O:22])=[O:21])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.Cl.C(=O)(O)[O-].[Na+]>CO.O1CCCC1.O1CCOCC1>[OH:39][C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[CH2:32][N:19]([S:20]([C:23]1[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=1[CH3:31])(=[O:22])=[O:21])[C:16]1[CH:15]=[CH:14][C:13]([CH:12]=[CH:11][C:10]([NH:9][CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[O:46])=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 69591893HCID 69591893, compound

Product 1

HCID 69591910HCID 69591910, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(2-pyridin-4-yl-ethyl)-3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-acrylamide (0.059 g, 0.09 mmol) in 0.4 mL methanol and 0.1 mL tetrahydrofuran was added HCl (0.5 mL of a 4.0 M solution in 1,4-dioxane, 2 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 (eluting with 10% methanol/methylene chloride) to afford 0.018 g of 3-{4-[(3-hydroxy-benzyl)-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-N-(2-pyridin-4-yl-ethyl)-acrylamide. 1H NMR (CDCl3) δ 8.32 (d, 2H, J=4.8 Hz), 7.27 (d, 1H, J=16.4 Hz), 7.18 (d, 2H, J=5.2 Hz), 7.03–6.98 (m, 4H), 6.90–6.86 (m, 4H), 6.69 (s, 2H), 6.60 (d, 1H, J=7.2 Hz), 6.24 (d, 1H, J=15.6 Hz), 4.67 (s, 2H), 3.62–3.57 (m, 2H), 2.88 (t, 2H, J=6.4 Hz), 2.41 (s, 6H), 2.24 (s, 3H).

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 (eluting with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-bc9a05edceb6417886852d587ecb0482
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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