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

HRID 1399788Notes

Reaction equation

HRID 1399788 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]([C:29]([F:32])([F:31])[F:30])[C:24]=1[CH3:33].C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[CH3:1][C:2]1[N:20]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[C:24]=2[CH3:33])[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 27756171-(Bromomethyl)-2-methyl-3-(trifluoromethyl)benzeneHCID 178498376methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate2×

Product 1

HCID 89648239methyl 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylateYield 95.1%

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 (207 mg, 0.75 mmol), 1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (285 mg, 1.125 mmol) and Na2CO3 (239 mg, 2.25 mmol) in DMF (10 mL) was stirred at 80° C. for 3 h. TLC showed no methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate left. It was cooled to room temperature and poured into water (50 mL) and filtered. The solid was dissolved with DCM (150 mL) and it was washed with brine (100 mL×3) and the organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the desired product as a brown solid (320 mg, 95%); LC/MS: MS (ES+) m/e 449 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.40 (s, 3H), 2.51 (s, 3H), 3.41 (t, J=4.8 Hz, 4H), 3.68 (t, J=4.8 Hz, 4H), 3.92 (s, 3H), 5.50 (s, 2H), 6.90 (d, J=7.8 Hz, 1H), 7.07 (s, 1H), 7.28 (t, J=7.5 Hz, 1H), 7.62 (d, J=7.8 Hz, 1H).

Workup

  1. waitleft
  2. temperatureIt was cooled to room temperature
  3. filtrationfiltered
  4. dissolutionThe solid was dissolved with DCM (150 mL) and it
  5. washwas washed with brine (100 mL×3)
  6. dry with materialthe organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-452e1e8490794fc69871dcb6970ea29a
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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