Phosphorus oxychloride → HCID 58382412, compound

HRID 1628062Notes

Reaction equation

HRID 1628062 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH2:20][NH:21][CH:22]=O)[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>ClCCCl>[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([CH:22]=[N:21][CH:20]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 58382230HCID 58382230, compound

Product 1

HCID 58382412HCID 58382412, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

N-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)formamide (3.66 g, 11.1 mmol, prepared using J.3 from Example #2, Step C with ethyl formate) was suspended in DCE (80 mL) then POCl3 (1.08 mL, 11.6 mmol) was added. The mixture was heated to about 80° C. for about 90 min and then cooled to rt. The mixture was treated with about 50 mL saturated aqueous NaHCO3 and then stirred for about 15 min. The layers were separated and aqueous layer was extracted with DCM (40 mL). The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure to give 6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (3.46 g, 100%): LC/MS (Table 2, Method a) Rt=1.97 min; MS m/z 313 (M+H)+.

Workup

  1. temperaturecooled to rt
  2. customThe layers were separated
  3. extractionaqueous layer was extracted with DCM (40 mL)
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7f848078b5ea4f40853804c936d8fd91
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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