Water → HCID 11494917, compound

HRID 1170490Notes

Reaction equation

HRID 1170490 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1)=O.C(OC(=O)[N:19]([CH2:34][CH2:35][NH2:36])[CH:20]([C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[N:23]=1)[CH3:21])(C)(C)C.O>O1CCOCC1.C(O)(C(F)(F)F)=O.C(Cl)Cl.CCOC(C)=O>[O:10]1[C:7]2[CH:8]=[CH:9][C:4]([CH:2]([NH:36][CH2:35][CH2:34][NH:19][CH:20]([C:22]3[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]4[CH:33]=[CH:32][N:31]=[CH:30]4)[N:23]=3)[CH3:21])[CH3:1])=[CH:5][C:6]=2[O:12][CH2:11]1

Participants

7

Reactant 3

HCID 962WaterHCID 76622AcetopiperoneHCID 68692721HCID 68692721, compound

Product 1

HCID 11494917HCID 11494917, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

3,4-(Methylenedioxy)acetophenone (95.0 mg, 577 μmol) and (2-amino-ethyl)-[1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-ethyl]-carbamic acid tert-butyl ester (200 mg, 577 μmol) were heated to 70° C. in 1,4-dioxane (4 mL) under a nitrogen atmosphere for 16 h. The reaction was then cooled to r.t. and NaHB(OAc)3 (367 mg, 1.73 mmol) was added. After stirring for an additional hour, water was added and the solution was extracted with ethyl acetate (2×50 mL), washed with brine and dried over Na2SO4. Evaporation of the solvent gave a yellow residue which was dissolved in TFA/DCM (1:1, 5 mL) and stirred at room temperature for 30 min. The solvent was evaporated to afford an orange residue. The crude product was diluted with EtOAc (50 mL), washed with 1M NaOH (50 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated to an oil. Purification was achieved using column chromatography (CH2Cl2 to 4:1 CH2Cl2/MeOH) to afford 198 mg (87%) of N-(1-benzo[1,3]dioxol-5-yl-ethyl)-N′-[1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-ethyl]-ethane-1,2-diamine as a clear glass. [M+H]+ 395.05; 1H NMR (400 MHz, CD3OD) δ 8.87 (s, 1H), 8.09 (s, 1H), 7.42 (s, 1H), 7.36 (s, 1H), 7.00 (d, 1H), 6.91 (dd, 1H), 6.78 (dd, 1H), 5.96 (s, 2H), 4.30 (q, 1H), 3.57 (m, 2H), 3.38 (q, 1H), 2.73 (m, 4H), 2.60 (s, 3H), 1.60 (d, 3H), 1.48 (d, 3H).

Workup

  1. extractionthe solution was extracted with ethyl acetate (2×50 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent
  5. customgave a yellow residue which
  6. stirringstirred at room temperature for 30 min
  7. customThe solvent was evaporated
  8. customto afford an orange residue
  9. washwashed with 1M NaOH (50 mL), brine (50 mL)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated to an oil
  13. customPurification

Sources & evidence

ORD record
ord-98d134204ddf4cfdbb75980b5984fe43
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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