Dimethylformamide → HCID 68752316, compound

HRID 1038834Notes

Reaction equation

HRID 1038834 reaction equation
[N:1]1[C:9]2[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][C:4]=2[NH:3][CH:2]=1.CN(C=O)C.[H-].[Na+].[S:24](Cl)([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>O.C(Cl)Cl>[S:24]([N:3]1[C:4]2[CH2:5][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][CH2:8][C:9]=2[N:1]=[CH:2]1)([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 57481540tert-Butyl 1H,4H,5H,6H,7H-imidazo[4,5-c]pyridine-5-carboxylate

Product 1

HCID 68752316HCID 68752316, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A flask was charged with tert-butyl 6,7-dihydro-3H-imidazo[4,5-c]pyridine-5(4H)-carboxylate (0.44 g, 2.0 mmol, WO2009158394, Example M-In-1) and DMF (10 mL). The mixture was cooled to about 0° C. and NaH (60% dispersion in mineral oil, 0.095 g, 2.4 mmol) was added. The mixture was stirred at about 0° C. for about 20 min followed by the addition of TsCl (0.41 g, 2.2 mmol). The resulting mixture was stirred at about 0° C. for about 90 min and then at about rt for about 3.5 h. The mixture was poured into DCM (40 mL) and water (20 mL) was added. The layers were separated and the organic solution was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0 to 50% EtOAc in DCM to give tert-butyl 3-tosyl-6,7-dihydro-3H-imidazo[4,5-c]pyridine-5(4H)-carboxylate (0.21 g, 28%): LC/MS (Table 2, Method n) Rt=2.53 min; MS m/z: 378 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred at about 0° C. for about 90 min
  2. waitat about rt for about 3.5 h
  3. additionwas added
  4. customThe layers were separated
  5. washthe organic solution was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by silica gel chromatography
  10. washeluting with a gradient of 0 to 50% EtOAc in DCM

Sources & evidence

ORD record
ord-df447e5e991a4f18a7fa6a60a60c0a7e
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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