Water → methyl 2-methyl-5-morpholino-3-(naphthalen-1-ylmethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylate

HRID 1399794Notes

Reaction equation

HRID 1399794 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[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[CH3:1][C:2]1[N:20]([CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[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]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 1378441-(Bromomethyl)naphthaleneHCID 178498376methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

Product 1

HCID 89648052methyl 2-methyl-5-morpholino-3-(naphthalen-1-ylmethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (138 mg, 0.5 mmol), 1-(bromomethyl)naphthalene (166 mg, 0.75 mmol) and Na2CO3 (138 mg, 1 mmol) in DMF (10 mL) was stirred at 80° C. for 5 h. It was cooled to room temperature and poured into water (50 mL). It was extracted with EA (100 mL×2). The combined organic layers were washed with brine (100 mL×2), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluted with 100% EA to afford the desired product as a black solid (143 mg, 69%); LC/MS: MS (ES+) m/e 417 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.42 (s, 3H), 3.42 (t, J=4.5 Hz, 4H), 3.67 (t, J=4.5 Hz, 4H), 3.93 (s, 3H), 5.92 (s, 2H), 6.70 (d, J=7.2 Hz, 1H), 7.09 (s, 1H), 7.39 (t, J=7.5 Hz, 1H), 7.57-7.65 (m, 2H), 7.87 (d, J=9.0 Hz, 1H), 7.90 (d, J=9.0 Hz, 1H), 8.34 (d, J=7.2 Hz, 1H).

Workup

  1. temperatureIt was cooled to room temperature
  2. extractionIt was extracted with EA (100 mL×2)
  3. washThe combined organic layers were washed with brine (100 mL×2)
  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 100% EA

Sources & evidence

ORD record
ord-289fa1ce279a4e86a48cb7a77028ee1a
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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