Dimethylformamide → HCID 10450788, compound

HRID 1791362Notes

Reaction equation

HRID 1791362 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[NH:17])[NH:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:25]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](Cl)=O)#[N:26].CN(C=O)C>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[N:17]=[C:30]([C:29]2[CH:33]=[CH:34][CH:35]=[C:27]([C:25]#[N:26])[CH:28]=2)[O:16][N:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 3084833-Cyanobenzoyl chlorideHCID 178451840HCID 178451840, compound

Product 1

HCID 10450788HCID 10450788, compoundYield 22.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a 50 mL round bottom flask equipped with stir bar, added 2-(N-hydroxycarbamimidoyl)-piperidine-1-carboxylic acid tert-butyl ester (327 mg, 1.34 mmol), dichloromethane (5 mL) and triethylamine (0.56 mL, 4.03 mmol). To this stirred mixture was added a solution of 3-cyanobenzoyl chloride (222 mg, 1.34 mmol) in dichloromethane (3 mL). The resulting reaction mixture was stirred at room temperature for 2 h. DMF (5 mL) was added to the reaction mixture and stirred at 120° C. for 2 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (50 mL). The organic phase was successively washed with water (30 mL) and brine (20 mL), dried (sodium sulfate), filtered and concentrated in vacuo. The crude residue was purified on silica gel using 20% ethyl acetate in hexanes to isolate 106 mg of the title compound as a white solid. 1H-NMR (CDCl3), δ(ppm): 8.42 (s, 1H), 8.35 (d, 1H), 7.86 (dd, 1H), 7.67 (t, 1H), 5.56 (bs, 1H), 4.11 (bd, 1H), 3.04 (bs, 1H), 2.32 (d, 1H), 1.97 (m, 1H), 1.69 (t, 1H), 1.48 (m, 12H).

Workup

  1. customIn a 50 mL round bottom flask equipped
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature for 2 h
  4. stirringstirred at 120° C. for 2 h
  5. washThe organic phase was successively washed with water (30 mL) and brine (20 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified on silica gel using 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-58507d49889e46be85380f27529308d1
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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