Water → HCID 44177707, compound

HRID 1898191Notes

Reaction equation

HRID 1898191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11](COC)[C:12]2[C:13]([C:19]([C:21]3[C:22]4[CH:29]=[N:28][NH:27][C:23]=4[N:24]=[CH:25][CH:26]=3)=[O:20])=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34].O>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([C:21]3[C:22]4[CH:29]=[N:28][NH:27][C:23]=4[N:24]=[CH:25][CH:26]=3)=[O:20])=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:33]([F:35])([F:34])[F:36]

Participants

5

Reactant 2

HCID 962WaterHCID 57942423HCID 57942423, compound

Product 1

HCID 44177707HCID 44177707, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-N-methoxymethyl-N-[5-methyl-2-(1H-pyrazolo[3,4-b]pyridine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (50 mg, 0.092 mmol) in 4M HCl in dioxane (4 mL) and water (1 mL) was stirred at 70° C. for overnight. Reaction mixture was cooled to room temperature, evaporated to dryness and treated with saturated aqueous NaHCO3 solution till pH 7-8. The mixture was extracted with EtOAc (2×25 mL), dried (anhydrous Na2SO4) and concentrated. The obtained residue was purified by flash chromatography (SiO2, 70% EtOAc-hexanes) to afford 4-chloro-N-[5-methyl-2-(1H-pyrazolo[3,4-b]pyridine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (28.9 mg) as yellow solid (after lyophilization) in 63% yield. 1H NMR (400 MHz, CDCl3) δ10.75 (s, 1H), 8.65 (d, 1H), 8.24 (m, 1H), 8.14 (d, 1H), 8.08 (s, 1H), 7.94-7.99 (m, 2H), 7.59 (d, 1H), 7.58 (d, 1H), 2.48 (s, 3H); ESMS m/z (relative intensity): 496 (M+H)+ (100).

Workup

  1. customReaction mixture
  2. customevaporated to dryness
  3. additiontreated with saturated aqueous NaHCO3 solution till pH 7-8
  4. extractionThe mixture was extracted with EtOAc (2×25 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated
  7. customThe obtained residue was purified by flash chromatography (SiO2, 70% EtOAc-hexanes)

Sources & evidence

ORD record
ord-ba353821779c483782442ebef0f490c2
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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