2-Chloro-3-cyclohexyl-3H-imidazo[4,5-b]pyridin-5-yl methanesulfonate → HCID 178515751, compound

HRID 1890359Notes

Reaction equation

HRID 1890359 reaction equation
CS([O:5][C:6]1[N:11]=[C:10]2[N:12]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:13]([Cl:15])=[N:14][C:9]2=[CH:8][CH:7]=1)(=O)=O>[Li+].[OH-].C1COCC1.CO>[Cl:15][C:13]1[N:12]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:10]2=[N:11][C:6]([OH:5])=[CH:7][CH:8]=[C:9]2[N:14]=1

Participants

3

Reactant 1

HCID 866552622-Chloro-3-cyclohexyl-3H-imidazo[4,5-b]pyridin-5-yl methanesulfonate

Product 1

HCID 178515751HCID 178515751, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 86635511LiOH methanol THFSolvent

Procedure

2-Chloro-3-cyclohexyl-3H-imidazo[4,5-b]pyridin-5-yl methanesulfonate (0.25 g, 0.758 mmol) was dissolved in 10 mL of a 1:4:1 of 1 M LiOH/THF/MeOH and stirred at room temperature for 1 h. The organic solvents were removed under reduced pressure and the remaining mixture was acidified with 1 M HCl to form a precipitate. The precipitate was collected, washed with water, and purified by HPLC to give the title compound (0.01 g). LCMS m/z=252.30 [M+H]+, 1H NMR (400 MHz, methanol-d4) δ ppm 1.39-1.43 (m, 1H), 1.45-1.54 (m, 2H), 1.8 (d, J=11.33 Hz, 1H), 1.88 (d, J=11.69 Hz, 2H), 1.98 (d, J=11.59 Hz, 2H), 2.59-2.69 (m, 2H), 4.52-4.59 (m, 1H), 6.64 (d, J=8.6 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H).

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. customto form a precipitate
  3. customThe precipitate was collected
  4. washwashed with water
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-9c071ef9df654883935bac8aa218736a
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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