Hydrochloric Acid → HCID 66727899, compound

HRID 573267Notes

Reaction equation

HRID 573267 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)=[CH:3]1.[Cl:18][C:19]1[O:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.Cl.O1CCOCC1>CN1CCCC1=O.CCOC(C)=O>[ClH:18].[CH3:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:17]=[CH:16][C:14]([NH:15][C:19]3[O:20][C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:13][CH:12]=2)=[CH:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 119862-ChlorobenzoxazoleHCID 312751,4-DioxaneHCID 86688956HCID 86688956, compound

Product 1

HCID 66727899HCID 66727899, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)aniline (70 mg) and 2-chlorobenzo[d]oxazole (57 mg) in 1-methylpyrrolidinone (2 mL) was stirred at 120° C. for 30 min. After this time, the reaction was cooled to room temperature, diluted with AcOEt (50 mL), washed with saturated NaHCO3 aqueous solution (50 mL), water (2×50 mL) then brine (50 mL), dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (CH2Cl2 to 1:19 MeOH/CH2Cl2), dissolved in 1,4-dioxane (2 ml), treated with 4 M HCl in 1,4-dioxane (0.500 mL, 2.00 mmol) and concentrated under reduced pressure. The residue obtained was triturated with boiling is CH3CN to give the title compound (60 mg).

Workup

  1. temperatureAfter this time, the reaction was cooled to room temperature
  2. washwashed with saturated NaHCO3 aqueous solution (50 mL), water (2×50 mL)
  3. dry with materialbrine (50 mL), dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by silica gel column chromatography (CH2Cl2 to 1:19 MeOH/CH2Cl2)
  8. dissolutiondissolved in 1,4-dioxane (2 ml)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue obtained
  11. customwas triturated with boiling

Sources & evidence

ORD record
ord-edfc902896d844938e2eeed2fb5adfad
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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