Diethyl Ether → HCID 58847306, compound

HRID 1272462Notes

Reaction equation

HRID 1272462 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:24]=[CH:23][C:22]([NH2:25])=[N:21][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[C:26](Cl)(=[O:28])[CH3:27].[CH2:30]([O:32]CC)[CH3:31]>FC(F)(F)C(O)=O.CO>[C:26]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:24]=[CH:23][C:22]([NH2:25])=[N:21][C:11]3=[N:12][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([O:20][C:30](=[O:32])[CH3:31])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 135428142HCID 135428142, compound

Product 1

HCID 58847306HCID 58847306, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

201.0 mg (0.5 mmol) of 2,3-bis(4-hydroxyphenyl)-pyrido[2,3-b]pyrazin-6-ylamine was dissolved in 10 ml of trifluoroacetic acid. 0.355 mL (5.0 mmol, 10.0 eq) of acetyl chloride was added via syringe to this mixture. Upon heating to 80° C. bubbling of the reaction mixture and evolution of HCl gas was observed. The reaction mixture was heated at 80° C. for 1 hr, at which point LC/MS indicated a complete conversion of the starting material to the di-acetate. Solvent was removed in vacuo to give brown solid. The solid was dissolved in 3.0 mL of methanol and this solution was added to 40 mL of diethyl ether. Upon standing for about an hour a brown precipitate was formed. It was centrifuged down, washed with 45 mL of diethyl ether twice and dried in vacuo to give 191.9 mg (79.0%) of the product as a light-brown solid. 98% purity by LC/MS (230 DAD). Mass-spec [ES+]=415.5. 1H NMR (MeOH-d4) 2.28 (6H, s), 7.10–7.12 (4H, d), 7.24–7.26 (1H, d), 7.48–7.50 (2H, d), 7.54–7.56 (2H, d), 8.24–8.26 (1H, d).

Workup

  1. custombubbling of the reaction mixture and evolution of HCl gas
  2. temperatureThe reaction mixture was heated at 80° C. for 1 hr, at which point LC/MS
  3. customSolvent was removed in vacuo
  4. customto give brown solid
  5. waitUpon standing for about an hour
  6. customa brown precipitate was formed
  7. washwashed with 45 mL of diethyl ether twice
  8. customdried in vacuo

Sources & evidence

ORD record
ord-e78c1acb38a6449491d5ae6149fd0e64
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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