Hydrochloric Acid → HCID 86621121, compound

HRID 601720Notes

Reaction equation

HRID 601720 reaction equation
[CH2:1]([N:5]([CH3:13])[C:6]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:14]I.C(N([CH2:21][CH3:22])CC)C.Cl.C([O:27][CH2:28][CH3:29])(=O)C>C(#N)C>[CH2:1]([N:5]([CH3:13])[C:6]([N:8]1[C:9]2=[N:10][CH:11]=[CH:22][CH:21]=[C:14]2[C:29]([CH:28]=[O:27])=[CH:12]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 40126890HCID 40126890, compound2×

Product 1

HCID 86621121HCID 86621121, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 9.76 g (54 mmol) of the compound from step I (1) dissolved in 100 mL of acetonitrile was treated with 11.5 g (81 mmol) of methyl iodide. The reaction solution was stirred for 16 h at rt, then concentrated to an oil. The crude imidazolium iodide was then redissolved in 70 mL of THF and 5.25 g (36 mmol) of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde from step I (2) was added, followed by triethylamine (72 mmol, 7.2 grams). The resulting solution was heated to 60° C. for 24 h, then cooled and poured into a solution of 0.1 N HCl. Ethyl acetate was added, and the organic layer was separated, dried with brine and concentrated. The crude product (12.3 g, 132%) of the desired title compound contained an unknown impurity which was removed at the next step. MS ESI (M+H)+=260.24. 1H NMR (500 MHz, CDCl3) δ ppm 0.76-1.06 (m, 3H) 1.18-1.35 (m, 2H) 1.43-1.57 (m, 2H) 1.58-1.81 (m, 2H) 2.97-3.19 (m, 3H) 7.29-7.32 (m, 1H) 8.13 (s, 1H) 8.45 (dd, J=4.73, 1.68 Hz, 1H) 8.58 (d, J=7.94 Hz, 1H) 10.03 (s, 1H)

Workup

  1. concentrationconcentrated to an oil
  2. dissolutionThe crude imidazolium iodide was then redissolved in 70 mL of THF
  3. temperatureThe resulting solution was heated to 60° C. for 24 h
  4. temperaturecooled
  5. customthe organic layer was separated
  6. dry with materialdried with brine
  7. concentrationconcentrated
  8. customwas removed at the next step

Sources & evidence

ORD record
ord-6c5ff1c1ad094807be45893cc121f1c0
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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