Phosphorus oxychloride → HCID 10338650, compound

HRID 751317Notes

Reaction equation

HRID 751317 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:16]3[CH:25]=[C:24]4[C:19]([N:20]=[CH:21][C:22](=O)[NH:23]4)=[CH:18][CH:17]=3)=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[N:12]=2)[CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:22]1[CH:21]=[N:20][C:19]2[C:24](=[CH:25][C:16]([C:9]3[C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=4)=[N:12][N:11]4[CH2:13][CH2:14][CH2:15][C:10]=34)=[CH:17][CH:18]=2)[N:23]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11724985HCID 11724985, compound

Product 1

HCID 10338650HCID 10338650, compoundYield 86%

Procedure

Dissolve 7-[2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-quinoxalin-2-one (Example 55b; 200 mg, 0.6 mmol) in phosphorus oxychloride (20 mL). Reflux the solution for 30 min. Evaporate in vacuo. Dissolve the residue in 3:1 chloroform/isopropyl alcohol (100 mL) and wash the solution with 5% aqueous ammonia solution, brine and water. Dry the organic phase over sodium sulfate. Filter and evaporate the solvents in vacuo to give the target product as a yellow solid 180 mg (86%). MS (electrospray, m/z) 362.2 (M+1).

Workup

  1. temperatureReflux the solution for 30 min
  2. customEvaporate in vacuo
  3. dissolutionDissolve the residue in 3:1 chloroform/isopropyl alcohol (100 mL)
  4. washwash the solution with 5% aqueous ammonia solution, brine and water
  5. dry with materialDry the organic phase over sodium sulfate
  6. filtrationFilter
  7. customevaporate the solvents in vacuo

Sources & evidence

ORD record
ord-bfe51e356e3845369f1f0e01dbf68821
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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