Hydrochloric Acid → HCID 67532287, compound

HRID 1713074Notes

Reaction equation

HRID 1713074 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[C:5]([C:7]1[C:15]2[CH:14]=[CH:13][C:12](=[O:16])[N:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[S:9][C:8]=1[C:23]#[N:24])=[O:6].[OH-:28].[Na+].Cl>CCO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[C:5]([C:7]1[C:15]2[CH:14]=[CH:13][C:12](=[O:16])[N:11]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:10]=2[S:9][C:8]=1[C:23]([NH2:24])=[O:28])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67532236HCID 67532236, compound

Product 1

HCID 67532287HCID 67532287, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 5 (127 mg, 0.34 mmol) and 0.25M sodium hydroxide(aq) (1.36 ml, 0.34 mmol) was heated to reflux in EtOH (20 ml) for 45 minutes. The solution was cooled to room temperature, 2M HCl(aq) (100 ml) added and the aqueous extracted with DCM (2×100 ml). The combined DCM extracts were dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica (0-10% EtOAc in DCM) to give the title compound as a white solid (125 mg, 95%). δH (CDCl3) 7.70 (1H, br s), 7.59-7.32 (8H, m), 7.05 (1H, d, J 9.7 Hz), 6.44 (1H, d, J 9.7 Hz), 2.37 (3H, s). LCMS (ES+) RT 3.00 minutes, 389 (M+H)+.

Workup

  1. extractionthe aqueous extracted with DCM (2×100 ml)
  2. dry with materialThe combined DCM extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by chromatography on silica (0-10% EtOAc in DCM)

Sources & evidence

ORD record
ord-6204e1157a444355a7d3852b3d3903c6
Source dataset
uspto-grants-2010_09
Patent number
US07795256B2

Reaction notes

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