Hydrochloric Acid → HCID 59811898, compound

HRID 2114076Notes

Reaction equation

HRID 2114076 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:17]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:16][N:15](COCC[Si](C)(C)C)[C:12]3=[N:13][CH:14]=2)=[CH:5][CH:4]=1.Cl.C([O-])(O)=O.[Na+]>C(O)C>[CH3:1][N:2]([CH3:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:17]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57830135HCID 57830135, compound

Product 1

HCID 59811898HCID 59811898, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 61 (0.017 g, 0.038 mmol), 10% hydrochloric acid (1 mL), and ethanol (1 mL) was heated at 80° C. for 30 minutes. The mixture was cooled and poured into saturated NaHCO3 solution and extracted with AcOEt. The organic extract was dried (MgSO4), concentrated and purified by means of preparative TLC with CH2Cl2:methanol as eluent to afford 62 (0.0047 g, 39%) as a tan solid. 1H NMR (400 MHz, CDCl3) δ 2.94 (s, 6H), 3.02-3.06 (m, 4H), 3.86-3.90 (m, 4H), 6.75-6.81 (m, 3H), 7.42-7.47 (m, 2H), 7.97 (d, J=0.21 Hz, 1H), 8.44 (d, J=0.21 Hz, 1H), 8.74 (bs, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with AcOEt
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by means of preparative TLC with CH2Cl2

Sources & evidence

ORD record
ord-dfdcb97293884f54b9b853d1c3272d78
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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