Water → HCID 67332327, compound

HRID 1886926Notes

Reaction equation

HRID 1886926 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=4)=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:24](Cl)(=[O:26])[CH3:25].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[N:21][CH:22]=4)=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 67331134HCID 67331134, compound

Product 1

HCID 67332327HCID 67332327, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To 5-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)pyridin-2-amine (96.5 mg, 0.30 mmol) in dry pyridine (3 mL) at room temperature was added acetyl chloride (26 μL, 0.36 mmol), and stirred at 80° C. for 40 h. After cooling, the mixture was poured into water to give a precipitate, which was filtered off. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 20:80 v/v to afford 45 mg (41%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. customto give a precipitate, which
  3. filtrationwas filtered off
  4. customThe resulting solid was purified by column chromatography
  5. washeluting with ethyl acetate/hexanes 20:80 v/v

Sources & evidence

ORD record
ord-c7592eddc10a40e3a57394fe85021523
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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