Hydrogen Bromide → HCID 59278430, compound

HRID 1361176Notes

Reaction equation

HRID 1361176 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([C@@H:11]([NH:14][C:15]([C:17]2[C:18]3[CH:25]=[N:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:19]=3[CH:20]=[N:21][CH:22]=2)=[O:16])[CH2:12][CH3:13])[CH:8]=[C:7]([O:33]C)[N:6]=1)(=[O:4])=[O:3].Br>O>[CH3:1][S:2]([C:5]1[NH:6][C:7](=[O:33])[CH:8]=[C:9]([C@@H:11]([NH:14][C:15]([C:17]2[C:18]3[CH:25]=[N:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:19]=3[CH:20]=[N:21][CH:22]=2)=[O:16])[CH2:12][CH3:13])[CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 59278196HCID 59278196, compound

Product 1

HCID 59278430HCID 59278430, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-methanesulfonyl-6-methoxy-pyridin-4-yl)-propyl]-amide (0.150 g, 310 mmol) in 48% aqueous hydrobromic acid (7.0 mL, 42 mmol) was warmed at 60° C. After 5 hours, the mixture was cooled to room temperature, diluted with water (25 mL) and extracted with ethyl acetate (4×20 mL). The combined organic layers were washed with saturated sodium bicarbonate (4×20 mL), brine (20 mL), dried over sodium sulfate and concentrated in vacuo. The crude material was triturated with ethyl acetate-ether to afford the title compound.

Workup

  1. extractionextracted with ethyl acetate (4×20 mL)
  2. washThe combined organic layers were washed with saturated sodium bicarbonate (4×20 mL), brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material was triturated with ethyl acetate-ether

Sources & evidence

ORD record
ord-284b8b46c5c341c095c7a03d8cd30fbe
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

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