Hydrochloric Acid → HCID 131733862, compound

HRID 708838Notes

Reaction equation

HRID 708838 reaction equation
[CH:1]1([S:4]([C:7]2[C:22]([F:23])=[CH:21][C:20]([N+:24]([O-])=O)=[CH:19][C:8]=2[CH2:9][N:10](C)[C:11](=O)OC(C)(C)C)(=[O:6])=[O:5])[CH2:3][CH2:2]1.O1CCOCC1.[ClH:33]>CO.[Pd]>[ClH:33].[CH:1]1([S:4]([C:7]2[C:8]([CH2:9][NH:10][CH3:11])=[CH:19][C:20]([NH2:24])=[CH:21][C:22]=2[F:23])(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118098713HCID 118098713, compound

Product 1

HCID 131733862HCID 131733862, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a fine suspension of 11D (985 mg, 2.54 mmol) in MeOH (10 mL) was added 10% Pd—C (50 mg, 0.047 mmol). The mixture was evacuated and flushed with hydrogen (3×), then was stirred under an atmosphere of hydrogen for 22 h. The reaction mixture was filtered and concentrated to afford a colorless solid. The solid was suspended in 4N HCl in dioxane (6 mL, 24.00 mmol). The suspension was stirred at rt for 1 h, then concentrated to give 11E (840 mg, 2.54 mmol, 100% yield) as an off-white solid. MS (ESI) m/z: 259.1 [M+1]+. 1H NMR (400 MHz, MeOD) δ ppm 6.60 (1H, d, J=2.0 Hz), 6.54 (1H, dd, J=13.6, 2.3 Hz), 4.31 (2H, s), 2.87-2.97 (1H, m), 2.75 (3H, s), 1.24-1.31 (2H, m), 1.05-1.13 (2H, m).

Workup

  1. customThe mixture was evacuated
  2. customflushed with hydrogen (3×)
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. customto afford a colorless solid
  6. stirringThe suspension was stirred at rt for 1 h
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c633f10684d14c20ac9dfea1ca790586
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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