Potassium Carbonate → HCID 136104419, compound

HRID 1919649Notes

Reaction equation

HRID 1919649 reaction equation
[C:1]1([NH:7][C:8]2[C:17]3[CH:18]=[CH:19][S:20][C:16]=3[C:15]3[CH:14]=[CH:13][C:12]([C:21]#[N:22])=[CH:11][C:10]=3[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:24]O.[C:26]([O-:29])([O-])=[O:27].[K+].[K+]>CCO>[C:1]1([NH:7][C:8]2[C:17]3[CH:18]=[CH:19][S:20][C:16]=3[C:15]3[CH:14]=[CH:13][C:12]([C:21]4[NH:24][C:26](=[O:27])[O:29][N:22]=4)=[CH:11][C:10]=3[N:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 50941655HCID 50941655, compound

Product 1

HCID 136104419HCID 136104419, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

4-(phenylamino)thieno[3,2-c]quinoline-7-carbonitrile (1.0 eq, 27 mg, 0.0897 mmol) and hydroxylamine hydrochloride (10 eq, 62 mg, 0.892 mmol) and K2CO3 (10 eq, 124 mg, 0.896 mmol) were mixed in EtOH (0.5 ml) and the mixture heated under microwave at 100° C. for 10 min. The solid were removed by filtration and washed with EtOH. The solvents were removed in vacuo. The crude material was suspended in chloroform (0.5 ml). Ethyl chloroformate (20 ul) and triethylamine (20 ul) were added and the mixture stirred at room temperature for 10 min. CH2Cl2 was added and the organic phase was washed with brine. The organic phase was dried over Na2SO4 and the solvent removed. The crude material was suspended in NMP (1 ml) and heated under microwave at 160° C. for 10 min. The material was purified by preparative HPLC. Genevac evaporation afforded 3-(4-(phenylamino)thieno[3,2-c]quinolin-7-yl)-1,2,4-oxadiazol-5(4H)-one as an off-white solid (7 mg, 22% yield). LCMS (ES): 95% pure, m/z 361 [M+1]+.

Workup

  1. customThe solid were removed by filtration
  2. washwashed with EtOH
  3. customThe solvents were removed in vacuo
  4. additionEthyl chloroformate (20 ul) and triethylamine (20 ul) were added
  5. additionCH2Cl2 was added
  6. washthe organic phase was washed with brine
  7. dry with materialThe organic phase was dried over Na2SO4
  8. customthe solvent removed
  9. temperatureheated under microwave at 160° C. for 10 min
  10. customThe material was purified by preparative HPLC
  11. customGenevac evaporation

Sources & evidence

ORD record
ord-9bf25fc03ec4447d894217bca252a4fd
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

Loading…