2-Methylpyrrolidine → HCID 87464554, compound

HRID 2245378Notes

Reaction equation

HRID 2245378 reaction equation
[I-].[F:2][C:3]1([F:27])[O:7][C:6]2[CH:8]=[CH:9][C:10]([N:12]3[CH2:16][C:15](=[CH2:17])[S:14]/[C:13]/3=[N:18]\[C:19](N3C=C[N+](C)=C3)=[O:20])=[CH:11][C:5]=2[O:4]1.[CH3:28][CH:29]1[CH2:33][CH2:32][CH2:31][NH:30]1.CCN(C(C)C)C(C)C>C(#N)C.C(Cl)Cl>[F:27][C:3]1([F:2])[O:7][C:6]2[CH:8]=[CH:9][C:10]([N:12]3[CH2:16][C:15](=[CH2:17])[S:14]/[C:13]/3=[N:18]\[C:19]([N:30]3[CH2:31][CH2:32][CH2:33][CH:29]3[CH3:28])=[O:20])=[CH:11][C:5]=2[O:4]1

Participants

6

Reactant 3

HCID 130032-MethylpyrrolidineHCID 81531DiisopropylethylamineHCID 87464251HCID 87464251, compound

Product 1

HCID 87464554HCID 87464554, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-({[(2Z)-3-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-methylene-1,3-thiazolidin-2-ylidene]amino}carbonyl)-3-methyl-1H-imidazol-3-ium iodide (Example 116, 0.1 g, 0.19 mmol) and 2-methylpyrrolidine (0.018 g, 0.19 mmol) in anhydrous acetonitrile (5 mL) was added Hunig's base (0.025 g), and then the solution was heated at 60° C. for 3 hours. After cooling to room temperature, the reaction was diluted with 50 mL of CH2Cl2, washed water and brine, dried over sodium sulfate, and evaporated under reduced pressure. The crude residue was choromatographed over silica using CH2Cl2 to give the titled compound. 1H NMR (CD3OD) δ ppm 1.00 (3H), 1.60 (1H), 1.90 (3H), 3.40 (2H), 3.90 (1H), 4.80 (2H), 5.20 (1H), 5.35 (1H), 7.30 (2H), 7.50 (1H); MS (ESI) 382(M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-babb32854164460d82197e8dff6f6469
Source dataset
uspto-grants-2010_03
Patent number
US07683084B2

Reaction notes

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