Water → HCID 57731972, compound

HRID 401744Notes

Reaction equation

HRID 401744 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[Cl:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[O:22][CH2:23][C@@H:24]1[CH2:28][CH2:27][CH2:26][NH:25]1.[C:32](=O)([O-])[O-:33].[Na+].[Na+].O>Cl.C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[O:22][CH2:23][C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:32]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1)=[O:33]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamideHCID 68534217HCID 68534217, compound

Product 1

HCID 57731972HCID 57731972, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178521658HCID 178521658, compoundCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-iodo-N-1,3-thiazol-2-ylbenzenesulfonamide (Preparation 98, 150 mg, 0.41 mmol), (2S)-2-(3-chloro-phenoxymethyl)-pyrrolidine hydrochloride (Preparation 90, 430 mg, 2.0 mmol), hexacarbonylmolybdenum (50 mg, 0.2 mmol), palladium(II) acetate (4 mg, 0.02 mmol), and sodium carbonate (130 mg, 1.2 mmol) in water (0.82 mL, 45 mmol) was heated 20 min at 110° C. in the microwave. The reaction mixture was diluted with 1 N HCl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was taken up in 1.2 mL of DMSO, filtered, and purified via HPLC (Prep: Phenomenex 250×30.0 mm 15 micron C18 column. 40 mL/min. Gradient 15% B to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered
  7. custompurified via HPLC (Prep: Phenomenex 250×30.0 mm 15 micron C18 column. 40 mL/min. Gradient 15% B to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA)

Sources & evidence

ORD record
ord-dc72073ce46d4fbc86ae40b01a14a287
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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