Hydrochloric Acid → HCID 69591927, compound

HRID 1827587Notes

Reaction equation

HRID 1827587 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[O:36])=[CH:29][CH:28]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]C3CCCCO3)=[CH:16][CH:15]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl>CO>[OH:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:12]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[O:36])=[CH:29][CH:28]=2)[S:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)(=[O:11])=[O:10])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69591925HCID 69591925, compound

Product 1

HCID 69591927HCID 69591927, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methoxy-N-[4-(3-morpholin-4-yl-3-oxo-propenyl)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide (0.028 g, 0.05 mmol) in 15 mL methanol was added 5 mL of 1N HCl. The reaction mixture was stirred at room temperature for 20 hr. The reaction mixture was washed twice with methylene chloride. The combined organic layers were washed with saturated aqueous sodium bicarbonate, dried (magnesium sulfate), and concentrated. Radial chromatography (methylene chloride to 5% methanol/methylene chloride) provided N-(4-hydroxy-benzyl)-4-methoxy-N-[4-(3-morpholin-4-yl-3-oxo-propenyl)-phenyl]-benzenesulfonamide. 1H NMR (CDCl3) δ 7.54 (d, 2H, J=9.2 Hz), 7.52 (d, 1H, J=15.2 Hz), 7.27 (d, 2H, J=8.4 Hz), 6.99 (d, 2H, J=8.4 Hz), 6.92 (d, 2H, J=8.8 Hz), 6.91 (d, 2H, J=9.2 Hz), 6.71 (d, 1H, J=15.2 Hz), 6.63 (d, 2H, J=8.4 Hz), 4.59 (s, 2H), 3.85 (s, 3H), 3.75–3.55 (m, 8H).

Workup

  1. washThe reaction mixture was washed twice with methylene chloride
  2. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c47e85b248344784872b709044590e38
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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