Propionic Acid → HCID 178493980, compound

HRID 707303Notes

Reaction equation

HRID 707303 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][C@H:13]3[CH2:16][C@H:15]([NH:17][C:18]4[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=4)[CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1.[C:25](OC)(OC)(OC)[O:26][CH3:27].C(O)(=O)CC>O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][C@H:13]3[CH2:16][C@H:15]([N:17]4[C:18]5=[N:19][CH:20]=[CH:21][CH:22]=[C:23]5[N:24]=[C:25]4[O:26][CH3:27])[CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 74613Tetramethyl orthocarbonateHCID 178507705HCID 178507705, compound

Product 1

HCID 178493980HCID 178493980, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

N2-(trans-3-((7-chloroquinoxalin-2-yl)amino)cyclobutyl)pyridine-2,3-diamine (118 mg, 0.346 mmol), tetramethyl orthocarbonate (922 μl, 6.92 mmol) and propionic acid (12.91 μl, 0.173 mmol) were combined under nitrogen. The reaction mixture was stirred at 100° C. for 2 hours. The reaction mixture was diluted with water and extracted with dichloromethane. The organic extract was washed with saturated ammonium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo to give the crude material as a off-white solid. It was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (4 g), eluting with a hexane to ethyl acetate gradient, to provide 7-chloro-N-(trans-3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)quinoxalin-2-amine (85 mg, 0.223 mmol, 64.5% yield). M+1: 380.9.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with saturated ammonium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated in vacuo
  6. customto give the crude material as a off-white solid
  7. customIt was absorbed onto a plug of silica gel
  8. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (4 g)
  9. washeluting with a hexane to ethyl acetate gradient

Sources & evidence

ORD record
ord-54ed61d34b82443f91b829a41844c84e
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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