Water → methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

HRID 1399790Notes

Reaction equation

HRID 1399790 reaction equation
[CH3:1][C:2]1[NH:20][C:5]2=[N:6][C:7]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:4]2[N:3]=1.Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[Cl:30].C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[Cl:30][C:24]1[C:25]([Cl:29])=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][N:20]1[C:5]2=[N:6][C:7]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:4]2[N:3]=[C:2]1[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27346021-(Bromomethyl)-2,3-dichlorobenzeneHCID 178498376methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

Product 1

HCID 89648260methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (200 mg, 0.72 mmol), 1-(bromomethyl)-2,3-dichlorobenzene), prepared as described in Example 3, step f, (259 mg, 1.08 mmol and Na2CO3 (229 mg, 2.16 mmol) in DMF (10 mL) was stirred at 80° C. for 16 h. The reaction mixture was cooled to room temperature and poured into water (100 mL). It was extracted with EtOAc (100 mL×2). The combined organic layers were washed with brine (100 mL×3), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluted with MeOH/DCM=1/60 to afford the desired product as a black solid (243 mg, 78%); LC/MS: MS (ES+) m/e 435 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.46 (s, 3H), 3.40 (t, J=4.2 Hz, 4H), 3.67 (t, J=4.2 Hz, 4H), 3.92 (s, 3H), 5.50 (s, 2H), 6.60 (d, J=7.8 Hz, 1H), 7.06 (s, 1H), 7.27 (t, J=7.8 Hz, 1H), 7.60 (d, J=7.8 Hz, 1H).

Workup

  1. customprepared
  2. extractionIt was extracted with EtOAc (100 mL×2)
  3. washThe combined organic layers were washed with brine (100 mL×3)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel
  8. washeluted with MeOH/DCM=1/60

Sources & evidence

ORD record
ord-9cb5fd774b1c4b26a6a186d6ff4574e6
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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