Hydrochloric Acid → HCID 178511870, compound

HRID 1922438Notes

Reaction equation

HRID 1922438 reaction equation
[O:1]=[C:2]1[CH:10]([CH:11]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:23][C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[NH:25])[CH:8]=2)[NH:3]1.Cl>CO>[O:1]=[C:2]1[CH:10]([CH:11]2[CH2:15][CH2:14][NH:13][CH2:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:23][C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[NH:25])[CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451782HCID 178451782, compound

Product 1

HCID 178511870HCID 178511870, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 5 (0.21 g, 0.492 mmol) in methanol (10 mL) was treated with 1 N HCl solution (10 mL) and the resulting solution was refluxed for 30 min. The reaction was brought to room temperature and solvent was evaporated. The crude was dissolved into water (10 mL), filtered and washed with water (2×5 mL). The combined water layer was evaporated to obtain compound 43 (0.173 g, 88%) as a solid. 1H NMR (DMSO-d6) δ 11.50 (brs, 1H), 10.87 (d, 1H, J=3.0 Hz), 9.79 (s, 1H), 9.69-9.46 (m, 2H), 8.80 (d, 1H, J=7.5 Hz), 8.19-8.16 (m, 2H), 7.43 (s, 1H), 7.37 (t, 1H, J=4.5 Hz), 7.30 (d, 1H, J=8.1 Hz), 7.01 (d, 1H, J=8.1 Hz), 3.50-3.32 (m, 1H), 3.30-3.02 (m, 3H), 2.75-2.50 (m, 2H), 2.18-2.08 (m, 1H), 1.96-1.40 (m, 1H); HPLC purity 95.52% by area.

Workup

  1. temperaturethe resulting solution was refluxed for 30 min
  2. customwas brought to room temperature
  3. customsolvent was evaporated
  4. dissolutionThe crude was dissolved into water (10 mL)
  5. filtrationfiltered
  6. washwashed with water (2×5 mL)
  7. customThe combined water layer was evaporated

Sources & evidence

ORD record
ord-c64afd18cfb24999853e1fb23cd069d7
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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