Pyridine → HCID 67353654, compound

HRID 1478902Notes

Reaction equation

HRID 1478902 reaction equation
[CH:1]1([CH2:4][N:5]2[C:13]3[CH:12]=[C:11]([NH:14][C:15](=[O:21])OC(C)(C)C)[N:10]=[CH:9][C:8]=3[CH:7]=[CH:6]2)[CH2:3][CH2:2]1.N1C=CC=CC=1.ClC([C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1)=O>Cl.O1CCOCC1>[CH:1]1([CH2:4][N:5]2[C:13]3[CH:12]=[C:11]([NH:14][C:15]([C:31]4[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=4)=[O:21])[N:10]=[CH:9][C:8]=3[CH:7]=[CH:6]2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 67353089HCID 67353089, compound

Product 1

HCID 67353654HCID 67353654, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (2C, 260 mg, 0.91 mmol) in 4M HCl in dioxane (3 ml) was stirred at room temperature for 15 h. The mixture was concentrated in vacuo and dissolved in pyridine (3 ml, 37 mmol). To the mixture, methyl 4-(chlorocarbonyl)benzoate (270 mg, 1.4 mmol) was added and stirred at room temperature for 3 hours. The mixture was extracted with EtOAc. 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-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamoyl)benzoate (2D, 270 mg, 0.77 mmol, 85% yield) as a white powder. 1 H NMR (400 MHz, DMSO-d6) δ ppm 0.39-0.47 (m, 2 H) 0.50-0.59 (m, 2 H) 1.17-1.33 (m, 1 H) 3.89 (s, 3 H) 4.06 (d, J=7.07 Hz, 2 H) 6.57-6.59 (m, 1 H) 7.52 (d, J=3.28 Hz, 1 H) 8.03-8.09 (m, 2 H) 8.14-8.19 (m, 2 H) 8.34 (s, 1 H) 8.65 (s, 1 H) 10.86 (s, 1 H). ESI-MS: m/z 350.0 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. stirringstirred at room temperature for 3 hours
  3. extractionThe mixture was extracted with EtOAc
  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-b47d0f6ee70b4f9b97fbe836de6dcdaa
Source dataset
uspto-grants-2016_08
Patent number
US09403819B2

Reaction notes

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