Pyridine → HCID 178440950, compound

HRID 1072000

Reaction equation

HRID 1072000 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:13]1[CH:18]=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25]C=1)=[O:21].C(N(C(C)C)CC)(C)C.C[N:42]([CH:44]=[O:45])C>C(Cl)Cl.CO>[C:44]([OH:45])(=[O:10])[C:20]([OH:22])=[O:21].[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:44]([N:42]2[CH2:23][CH2:28][C:27]3[NH:13][CH:18]=[N:29][C:26]=3[CH2:25]2)=[O:45])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 134164-tert-Butylbenzyl alcoholHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 178440950HCID 178440950, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-tert-butylbenzyl alcohol (1.97 g, 12 mmol) in DCM (30 mL) was added pyridine (1.3 mL) and then a solution of 4-nitrophenyl chloroformate (1.57 g, 7.8 mmol) in DCM (20 mL). The mixture was stirred at room temperature for 1 h, concentrated under reduced pressure, and to the residue was added a mixture of of 4,5,6,7-tetrahydromidazo[4,5-c]pyridine (1.5 g, 7 mmol), methanol (3.3 mL), DMF (30 mL), and diisopropylethylamine (4.1 mL). The resulting mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was distributed between water and ethyl acetate, phases were separated, and the organic layer was washed with water, dried (MgSO4), and filtered. A solution of oxalic acid (0.63 g) in ethyl acetate was added to the filtrate and the mixture was allowed to stand for 24 h. Filtration yielded the title compound as colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionto the residue was added
  3. stirringThe resulting mixture was stirred at room temperature overnight
  4. concentrationconcentrated under reduced pressure
  5. customwere separated
  6. washthe organic layer was washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. additionA solution of oxalic acid (0.63 g) in ethyl acetate was added to the filtrate
  10. waitto stand for 24 h
  11. filtrationFiltration

Sources & evidence

ORD record
ord-597b2f8d88f84ce8a7442fc7e07d1de4
Source dataset
uspto-grants-2005_06
Patent number
US06908926B1

Linked notes

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