Methanol → HCID 44177933, compound

HRID 1898284Notes

Reaction equation

HRID 1898284 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[C:22]([C:24]2[C:25]3[CH:32]=[CH:31][N:30]([Si](C(C)(C)C)(C)C)[C:26]=3[N:27]=[CH:28][CH:29]=2)=[O:23])COC)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:40]([F:43])([F:42])[F:41].O.CO>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[C:22]([C:24]2[C:25]3[CH:32]=[CH:31][NH:30][C:26]=3[N:27]=[CH:28][CH:29]=2)=[O:23])(=[O:9])=[O:10])=[CH:4][C:3]=1[C:40]([F:43])([F:41])[F:42]

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 58268180HCID 58268180, compound

Product 1

HCID 44177933HCID 44177933, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-N-[5-chloro-2-(1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonyl)-phenyl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (20 mg, 0.029 mmol) in 4N HCl in dioxane (2 mL) and water (0.5 mL) was stirred at 70° C. for overnight. MeOH (0.5 mL) was added and further stirred at the same temperature for 30 min. Then 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 HPLC to afford 4-chloro-N-[5-chloro-2-(1H-pyrrolo[2,3-b]pyridine-4-carbonyl)-phenyl]-3-trifluoromethyl-benzenesulfonamide in 60% yield. ESMS m/z (relative intensity): 514 (M+H)+ (100).

Workup

  1. customThen reaction 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 HPLC

Sources & evidence

ORD record
ord-bc51de883eef4cd98bedd7fa431ad17e
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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