Phosphorus oxychloride → HCID 178427995, compound

HRID 505569Notes

Reaction equation

HRID 505569 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]([NH: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>>[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][N:13]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428596HCID 178428596, compound

Product 1

HCID 178427995HCID 178427995, compound

Conditions

Temperature
120 °C

Procedure

A mixture of N′-[3-(3-bromo-5-chlorophenoxy)-4-methylpyridin-2-yl]-2-(1H-pyrazolo[3,4-b]pyridin-3-yl)acetohydrazide (44 mg, 0.090 mmol) in phosphorus oxychloride (250 μL, 2.6 mmol) was heated to 120° C. for 35 minutes, after which the excess reagent was removed in vacuo and the residue partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (2×20 mL). The combined extracts were concentrated in vacuo and the residue was purified on a Luna column (10μ, C18, 250×21.2 cm) eluting with 5-95% ACN/water with 0.1% TFA) to give the title compound. LRMS (M+1)=470.7.

Workup

  1. customafter which the excess reagent was removed in vacuo
  2. customthe residue partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (2×20 mL)
  3. concentrationThe combined extracts were concentrated in vacuo
  4. customthe residue was purified on a Luna column (10μ, C18, 250×21.2 cm)
  5. washeluting with 5-95% ACN/water with 0.1% TFA)

Sources & evidence

ORD record
ord-6dca4072721f4602be7dae258adb3ee3
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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