Carbon Disulfide → HCID 68663131, compound

HRID 452768Notes

Reaction equation

HRID 452768 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[NH:21][C:12]3[N:13]=[CH:14][CH:15]=[C:16]([C:17]([NH:19][NH2:20])=[O:18])[C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:29](=[S:31])=S.C(=O)([O-])[O-].[K+].[K+].[F:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42]Cl>C(O)C.C(OCC)(=O)C>[F:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42][S:31][C:29]1[O:18][C:17]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:21][C:9]([CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:10][C:11]=23)=[N:19][N:20]=1

Participants

8

Reactant 5

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 99743-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 68663654HCID 68663654, compound

Product 1

HCID 68663131HCID 68663131, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-phenylethyl)-1H-pyrrolo[2,3-b]pyridine-4-carbohydrazide (126 mg, 0.449 mmol), triethylamine (0.156 mL, 1.122 mmol) and carbon disulfide (0.136 mL, 2.246 mmol) in ethanol (10 mL) was stirred at 90° C. for 20 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in N,N-dimethylformamide (5 mL). To this solution were added potassium carbonate (93 mg, 0.674 mmol) and 3-fluorobenzyl chloride (0.065 mL, 0.539 mmol), and the resulting mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1) and basic silica gel column chromatography (hexane/ethyl acetate=9/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (44 mg, yield 23%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in N,N-dimethylformamide (5 mL)
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1) and basic silica gel column chromatography (hexane/ethyl acetate=9/1-0/1)
  7. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-1134442b8a0744c99e7e711330f9dcc1
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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