Sodium Nitrite → HCID 178494543, compound

HRID 1724855Notes

Reaction equation

HRID 1724855 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6](N)[C:7]2[C:8]([N:23]=1)=[N:9][C:10]([C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:11][N:12]=2.N([O-])=[O:26].[Na+]>C(O)(=O)C.O>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:26])[C:7]2[C:8]([N:23]=1)=[N:9][C:10]([C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:11][N:12]=2

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 57561041HCID 57561041, compound

Product 1

HCID 178494543HCID 178494543, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

6-Methoxymethyl-3-(3-trifluoromethyl-pyridin-2-yl)-pyrido-[2,3-b]pyrazin-8-ylamine (252 mg, 0.751 mmol) is dissolved in a solution of acetic acid (2 mL) and water (5 mL). The mixture is heated to 50° C. and sodium nitrite (362 mg, 5.26 mmol) is added in portions over 1 hour. The solution is warmed to 70° C. and stirred overnight. Water (20 mL) is added and the aqueous mixture is extracted with EtOAc (4×50 mL). The combined organic extracts are washed with brine and dried over Na2SO4. The solvent is removed under reduced pressure. The crude product is chromatographed on silica gel eluting with hexanes/acetone (1:1) to afford the title compound as a white solid.

Workup

  1. temperatureThe solution is warmed to 70° C.
  2. extractionthe aqueous mixture is extracted with EtOAc (4×50 mL)
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed under reduced pressure
  6. customThe crude product is chromatographed on silica gel eluting with hexanes/acetone (1:1)

Sources & evidence

ORD record
ord-434ab8575dc646fbbcbd1e6d41d4423c
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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