Hydrochloric Acid → HCID 21084002, compound

HRID 347927Notes

Reaction equation

HRID 347927 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:24](C(OCC)=O)[S:25][C:17]3=4)=[CH:12][CH:11]=2)[CH:4]=[CH:5][N:6]=1.Cl>O1CCOCC1.[OH-].[Na+]>[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:24][S:25][C:17]3=4)=[CH:14][CH:15]=2)[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21084055HCID 21084055, compound

Product 1

HCID 21084002HCID 21084002, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound of Example 91 (60 mg, 0.12 mmol) in dioxane (1 mL) was added 4M HCl(aq) (1 mL) and the mixture heated at reflux for 48 h. Reaction was diluted with 2M NaOH(aq) (5 mL) and extracted with DCM (2×10 mL). The combined DCM extracts were dried (MgSO4), filtered and concentrated in vacuo. The resultant solid was dried at 60° in a vacuum oven to afford the title compound (32 mg, 62%). δH (CDCl3) 7.76 (1H, d, J 9.6 Hz), 7.42–7.30 (6H, m), 7.00–6.92 (4H, m), 6.76 (1H, s), 6.58 (1H, d, J 9.6 Hz), 4.26–4.20 (4H, m), 2.46 (3H, s). LCMS (ES+) RT 2.48 minutes, 428 (M+H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 48 h
  3. customReaction
  4. extractionextracted with DCM (2×10 mL)
  5. dry with materialThe combined DCM extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant solid was dried at 60° in a vacuum oven

Sources & evidence

ORD record
ord-930f5c3e997e454ab5bf8fb42b04d9ab
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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