Phosphorus oxychloride → HCID 178518698, compound

HRID 2377766Notes

Reaction equation

HRID 2377766 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12](=[O:18])[NH:13][CH:14]=[CH:15][C:16]=1[I:17])=O.O=P(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[NH:1]1[C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N:8]=[C:9]1[C:11]1[C:12](=[O:18])[NH:13][CH:14]=[CH:15][C:16]=1[I:17]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 58819968HCID 58819968, compound

Product 1

HCID 178518698HCID 178518698, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-iodo-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid (4-amino-pyridin-3-yl)-amide (281 mg, 0.79 mmol) in 9 mL pyridine at 0 C was added (slowly) 0.5 mL POCl3 (5.3 mmol). The mixture was stirred at 0 C for 2 hours, then poured on a mixture of ice and saturated aqueous sodium bicarbonate solution. The product precipitates as a colloid. All attempts to filter or extract the product failed. The mixture was concentrated in vacuum, water removed by aceotropic destillation with n-propanol and the crude mixture used as it is. LCMS [M+H]+ 339, T=0.54 min product and [M+H]+ 357, T=0.29 min unreacted starting material [YMC ODS-A C18 S7 3.0×50 mm column; 0-100% gradient over 2 min*; 5 mL/min flow rate]. * Gradient begins with 10% methanol/90% water (0.1% TFA) and end with 90% methanol/10% water (0.1% TFA)

Workup

  1. customThe product precipitates as a colloid
  2. filtrationAll attempts to filter
  3. extractionextract the product
  4. concentrationThe mixture was concentrated in vacuum, water
  5. customremoved by aceotropic destillation with n-propanol
  6. customLCMS [M+H]+ 339, T=0.54 min product and [M+H]+ 357, T=0.29 min
  7. custommaterial [YMC ODS-A C18 S7 3.0×50 mm column; 0-100% gradient over 2 min*; 5 mL/min flow rate]

Sources & evidence

ORD record
ord-b6402c6b5a9348b7af9a6f8f556737e5
Source dataset
uspto-grants-2008_12
Patent number
US07470696B2

Reaction notes

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