Water → HCID 58577747, compound

HRID 587597Notes

Reaction equation

HRID 587597 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:19]([CH2:20][CH2:21]O)[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.O>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:11]3=[N:12][C:13]4[C:14](=[N:15][CH:16]=[CH:17][CH:18]=4)[N:19]3[CH2:20][CH2:21]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 58577698HCID 58577698, compound

Product 1

HCID 58577747HCID 58577747, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-{2-[(4-nitrophenyl)amino]-3H-imidazo[4,5-b]pyridin-3-yl}ethanol (2.2 g) and triethylamine (10 mL) in THF (100 mL) was added methanesulfonyl chlorode (1.1 mL) at 0° C., and the mixture was stirred at 0° C. for 2 h. The mixture was poured into water and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. A mixture of the residue and potassium carbonate (3.1 g) in NMP (30 mL) was stirred at 100° C. overnight. After cooling to room temperature, the mixture was diluted with water. The formed crystals were collected by filtration to give the title compound (1.7 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionA mixture of the residue and potassium carbonate (3.1 g) in NMP (30 mL)
  7. stirringwas stirred at 100° C. overnight
  8. temperatureAfter cooling to room temperature
  9. additionthe mixture was diluted with water
  10. filtrationThe formed crystals were collected by filtration

Sources & evidence

ORD record
ord-2dd3e2af9bb84000a02467cd28fcb30b
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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