Pyridine → HCID 67355294, compound

HRID 2405103Notes

Reaction equation

HRID 2405103 reaction equation
[CH3:1][S:2]([CH2:5][N:6]1[C:14]2[CH:13]=[C:12]([NH:15][C:16](=[O:22])OC(C)(C)C)[N:11]=[CH:10][C:9]=2[CH:8]=[CH:7]1)(=[O:4])=[O:3].N1C=CC=CC=1.ClC([C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1)=O>Cl.O1CCOCC1>[CH3:1][S:2]([CH2:5][N:6]1[C:14]2[CH:13]=[C:12]([NH:15][C:16]([C:32]3[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=3)=[O:22])[N:11]=[CH:10][C:9]=2[CH:8]=[CH:7]1)(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 67355878HCID 67355878, compound

Product 1

HCID 67355294HCID 67355294, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl 1-(methylsulfonylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (8D, 420 mg, 1.3 mmol) in 4M HCl in dioxane (3 ml) was stirred at 50° C. for 3 h. The mixture was concentrated in vacuo and the resulting residue was dissolved in pyridine (3 ml, 37.1 mmol). To the mixture, methyl 4-(chlorocarbonyl)benzoate (385 mg, 1.936 mmol) was added and stirred at room temperature for 3 h. The mixture was extracted with EtOAc/H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude mixture was purified by chromatography (NH—SiO2, EtOAc) to give methyl 4-(1-(methylsulfonylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamoyl)benzoate (8E, 160 mg, 0.40 mmol, 31% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.02 (s, 3H) 3.90 (s, 3H) 5.88 (s, 2H) 6.73 (d, J=2.78 Hz, 1H) 7.49 (d, J=3.28 Hz, 1H) 8.01-8.12 (m, 2H) 8.12-8.19 (m, 2H) 8.46 (s, 1H) 8.70 (s, 1H) 10.93 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. stirringstirred at room temperature for 3 h
  3. extractionThe mixture was extracted with EtOAc/H2O
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was purified by chromatography (NH—SiO2, EtOAc)

Sources & evidence

ORD record
ord-9b031e3716bf4a199a25930dc7c40612
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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