Phosphorus oxychloride → HCID 178427994, compound

HRID 505563Notes

Reaction equation

HRID 505563 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[O:5][C:6]1[C:7]([CH2:13][NH:14][C:15](=O)[CH2:16][C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[NH:19][N:18]=2)=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[O:5][C:6]1[C:7]2[N:8]([C:15]([CH2:16][C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[NH:19][N:18]=3)=[N:14][CH:13]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428520HCID 178428520, compound

Product 1

HCID 178427994HCID 178427994, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of N-{[3-(3-bromo-5-chlorophenoxy)-4-methylpyridin-2-yl]methyl}-2-(1H-pyrazolo[3,4-b]pyridin-3-yl)acetamide (77 mg, 0.158 mmol) in toluene (2 mL) was added phosphorus oxychloride (120 μL, 0.79 mmol). The resulting mixture was then heated at 100° C. for 1 hour, after which the solvent was removed in vacuo and the residue was stirred with CH2Cl2 (50 mL) and saturated aqueous Na2CO3 (30 mL) for 30 minutes. The layers were partitioned and the organic extract was dried over MgSO4, filtered and the solvent removed in vacuo. This residue was purified using RediSep column (12 g) eluting with a gradient of 0-10% MeOH/CH2Cl2. The pure fractions were combined and the solvent removed in vacuo to give the title compound. LRMS (M+1)=469.7.

Workup

  1. customafter which the solvent was removed in vacuo
  2. customThe layers were partitioned
  3. extractionthe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThis residue was purified
  8. washeluting with a gradient of 0-10% MeOH/CH2Cl2
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1e1557031aa244baa5076dd2e14389d7
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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