tert-Butyl methyl ether → HCID 66795672, compound

HRID 723636Notes

Reaction equation

HRID 723636 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][C:11]1[CH:23]=[CH:22][C:14]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=1.CN(C(ON1N=[N:39][C:34]2[CH:35]=[CH:36][CH:37]=N[C:33]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC([O:52]C)(C)C>C(Cl)Cl>[CH2:20]([O:19][C:17](=[O:18])/[CH:16]=[CH:15]/[C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:33]([C:34]2([NH2:39])[CH2:37][CH2:36][CH2:35]2)=[O:52])=[CH:23][CH:22]=1)[CH3:21]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 81531DiisopropylethylamineHCID 97826Ethyl 3-(4-aminophenyl)acrylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 66795672HCID 66795672, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The acid from above (0.519 g, 2.0 mmol) was dissolved in DCM (10 mL). DIEA (1.39 mL, 8.0 mmol, 4 equivalents) was added, followed by ethyl 4-aminocinnamate (0.573 g, 3.0 mmol, 1.5 equivalent) and HATU (1.143 g, 3.0 mmol, 1.5 equivalents). The mixture was stirred at room temperature for 3 days. The reaction was poured into TBME (100 mL) and the solution washed successively with 10% aqueous citric acid (2×25 mL) and saturated aqueous NaHCO3 (25 mL), and dried over MgSO4. The solvent was removed under reduced pressure and the residue stirred with TFA (10 mL) for 30 min. Volatiles were then removed under reduced pressure and the residue was co-evaporated twice with hexane. The crude product was dissolved in TBME (60 mL) and the solution washed with 1N NaOH (2×25 mL). After drying (Na2SO4), volatiles were removed in vacuum to give the title compound as a light brown solid (0.500 g).

Workup

  1. washthe solution washed successively with 10% aqueous citric acid (2×25 mL) and saturated aqueous NaHCO3 (25 mL)
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. stirringthe residue stirred with TFA (10 mL) for 30 min
  5. customVolatiles were then removed under reduced pressure
  6. dissolutionThe crude product was dissolved in TBME (60 mL)
  7. washthe solution washed with 1N NaOH (2×25 mL)
  8. dry with materialAfter drying (Na2SO4), volatiles
  9. customwere removed in vacuum

Sources & evidence

ORD record
ord-40b8f62dddeb49eabda5055c73f2c27f
Source dataset
uspto-grants-2006_11
Patent number
US07141574B2

Reaction notes

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