Hydrochloric Acid → HCID 59807055, compound

HRID 1922445Notes

Reaction equation

HRID 1922445 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([CH:11]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]3)[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl>CO>[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([CH:11]3[CH2:15][CH2:14][NH:13][CH2:12]3)[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59807072HCID 59807072, compound

Product 1

HCID 59807055HCID 59807055, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 3 (2.2 g, 5.56 mmol) in methanol (solvent grade, 25 mL) was treated with 1 N HCl (40 mL) and the resulting mixture was refluxed for 30 minutes. The reaction was brought to room temperature, methanol was evaporated and the solution basified with 6 N NaOH (pH ˜14). The product was extracted into CH2Cl2 (3×50 mL) and the combined organic layers were dried (Na2SO4) and concentrated to give crude product 4 (1.49 g, 91%) as a syrup. 1H NMR (DMSO-d6) δ 1.47-1.62 (m, 6H), 1.97-2.08 (m, 1H), 2.59-2.68 (m, 3H), 2.73-2.79 (m, 2H), 2.84-2.88 (m, 2H), 3.08-3.09 (m, 1H), 3.78-3.87 (m, 1H), 6.85 (d, 1H, J=8.4 Hz), 7.22 (dd, 1H, J=2.4, 8.4 Hz), 7.26 (d, 1H, J=2.4 Hz); ESI-MS (m/z, %): 297, 295 (M+, 100).

Workup

  1. temperaturethe resulting mixture was refluxed for 30 minutes
  2. customwas brought to room temperature
  3. custommethanol was evaporated
  4. extractionThe product was extracted into CH2Cl2 (3×50 mL)
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-772f5b8b21d24254bb27b4d038409ad0
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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