Water → HCID 11689021, compound

HRID 1170492Notes

Reaction equation

HRID 1170492 reaction equation
C(OC(=O)[N:7]([CH2:12][C:13]1[CH:21]=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[CH:14]=1)[CH2:8][CH2:9][NH:10][CH3:11])(C)(C)C.Cl[C:24]1[S:28][N:27]=[C:26]([N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[N:25]=1.O>CS(C)=O.CCOC(C)=O>[O:17]1[C:16]2[CH:20]=[CH:21][C:13]([CH2:12][NH:7][CH2:8][CH2:9][N:10]([C:24]3[S:28][N:27]=[C:26]([N:29]4[CH:33]=[CH:32][N:31]=[CH:30]4)[N:25]=3)[CH3:11])=[CH:14][C:15]=2[O:19][CH2:18]1

Participants

6

Reactant 3

HCID 962WaterHCID 452743615-Chloro-3-(1H-imidazol-1-yl)-1,2,4-thiadiazoleHCID 68691647HCID 68691647, compound

Product 1

HCID 11689021HCID 11689021, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzo[1,3]dioxol-5-ylmethyl-(2-methylamino-ethyl)-carbamic acid tert-butyl ester (200 mg, 649 μmol), 5-chloro-3-imidazol-1-yl-[1,2,4]thiadiazole (121 mg, 649 μmol) and TEA (181 μL, 1.30 mmol) in DMSO (6 mL) was stirred at r.t. for 21 h. Water (50 mL) was added and the solution was extracted with ethyl acetate (2×25 mL), washed with brine, dried over Na2SO4, filtered and concentrated to a clear oil. The crude residue was dissolved in TFA/DCM (1:1, 4 mL) and stirred at room temperature for 30 min. The solvent was evaporated to afford an orange oil. 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 21.3 mg (9%) of N′-benzo[1,3]dioxol-5-ylmethyl-N-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-N-methyl-ethane-1,2-diamine as a white solid. [M+H]+ 358.92; 1H NMR (400 MHz, CDCl3) δ 8.30 (s, 1H), 7.64 (s, 1H), 7.07 (s, 1H), 6.81 (s, 1H), 6.73 (m, 2H), 5.92 (s, 2H), 3.76 (s, 3H), 3.65 (br s, 1H), 3.14 (m, 4H), 2.95 (t, 2H).

Workup

  1. extractionthe solution was extracted with ethyl acetate (2×25 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a clear oil
  6. dissolutionThe crude residue was dissolved in TFA/DCM (1:1, 4 mL)
  7. customThe solvent was evaporated
  8. customto afford an orange oil
  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-ed58611ac2f745ad8ec021fd47f3bb7c
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

Loading…