tert-Butanol → HCID 22024576, compound

HRID 1793087Notes

Reaction equation

HRID 1793087 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15](C(O)=O)=[C:16]([CH2:18][CH3:19])[N:17]=2)[CH:12]=[CH:13][N:14]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[C:47]([OH:51])([CH3:50])([CH3:49])[CH3:48]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([NH:42][C:45](=[O:30])[O:51][C:47]([CH3:50])([CH3:49])[CH3:48])=[C:16]([CH2:18][CH3:19])[N:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22024589HCID 22024589, compound

Product 1

HCID 22024576HCID 22024576, compound

Procedure

The resulting 8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazine-3-carboxylic acid was dissolved in tert-butyl alcohol (15 mL), then diphenylphosphorylazide (0.69 mL, 3.2 mmol) and triethylamine (0.49 mL, 3.5 mmol) were added thereto, and the mixture was stirred for 2 hours by heating under reflux. After being cooled to room temperature, the reaction mixture was evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2) to give the title compound (0.85 g) as a white amorphous.

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. customthe reaction mixture was evaporated
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-cf2dfacaa1cf4bf29ee8cbdd73c6f90d
Source dataset
uspto-grants-2006_07
Patent number
US07078405B2

Reaction notes

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