Sodium Carbonate → [6-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-benzooxazol-5-yl-amine

HRID 746461Notes

Reaction equation

HRID 746461 reaction equation
O1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[C:12]4[N:13]([CH:18]=[CH:19][N:20]=4)[CH:14]=[C:15](Br)[N:16]=3)[CH:8]=[CH:9][C:4]=2N=C1.S(O)(O)(=O)=O.[NH2:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.[NH2:36][C:37]1C=C(B(O)O)C=CC=1.C([O-])([O-])=[O:47].[Na+].[Na+]>COCCOC>[NH2:26][C:27]1[CH:28]=[C:29]([C:15]2[N:16]=[C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]4[O:47][CH:37]=[N:36][C:5]=4[CH:6]=3)[C:12]3[N:13]([CH:18]=[CH:19][N:20]=3)[CH:14]=2)[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 162111393-Aminophenylboronic Acid HemisulfateHCID 57447606Benzooxazol-6-yl-(6-bromo-imidazo[1,2-a]pyrazin-8-yl)-amine

Product 1

HCID 57447607[6-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-benzooxazol-5-yl-amine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

A quantity of 0.33 g (1 mmole) of benzooxazol-6-yl-(6-bromo-imidazo[1,2-a]pyrazin-8-yl)-amine is dissolved in 10 mL ethylene glycol dimethyl ether and the solution purged for 15 minutes with N2. Catalytic tetrakis(triphenylphosphine)palladium (10 mol %) is added and the solution purged with N2 for 5 minutes with vigorous stirring. 3-Aminophenylboronic acid hemisulfate (0.23 g, 1.25 mmole) is added to the reaction, followed by 4 mL of 1.0N Na2CO3 and the reaction heated to 95° C. overnight in a sealed tube. The reaction is then cooled to rt, and the bilayer partitioned between ethyl acetate and water. The water layer is further extracted with ethyl acetate, and the organic extracts are pooled and washed with brine. After drying the organic extracts with solid sodium sulfate, the solvents are removed in vacuo to afford the [6-(3-amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-benzooxazol-5-yl-amine, which is purified by silica chromatography.

Workup

  1. customthe solution purged for 15 minutes with N2
  2. additionCatalytic tetrakis(triphenylphosphine)palladium (10 mol %) is added
  3. customthe solution purged with N2 for 5 minutes with vigorous stirring
  4. temperatureThe reaction is then cooled to rt
  5. customthe bilayer partitioned between ethyl acetate and water
  6. extractionThe water layer is further extracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialAfter drying the organic extracts with solid sodium sulfate
  9. customthe solvents are removed in vacuo

Sources & evidence

ORD record
ord-a5c502ba464b4e24b4fb38b8f0545096
Source dataset
uspto-grants-2008_07
Patent number
US07393848B2

Reaction notes

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