N,N'-Dimethylethylenediamine → HCID 52935645, compound

HRID 1423028Notes

Reaction equation

HRID 1423028 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[N:14]([C:18]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[N:19][CH:20]=3)[CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1.[CH3:28][S:29]([O-:31])=[O:30].[Na+].CNCCNC>CS(C)=O.[Cl-].[NH4+].FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[CH3:28][S:29]([C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[N:14]([C:18]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[N:19][CH:20]=3)[CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1)(=[O:31])=[O:30]

Participants

7

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 52935644HCID 52935644, compound

Product 1

HCID 52935645HCID 52935645, compound

Reagents, catalysts & solvents 3

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 679Dimethyl SulfoxideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-(4-fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid (6-bromopyridin-3-ylmethyl)-amide (133 mg, 0.313 mmol) in DMSO (2 mL) in a microwave tube is added sodium methanesulfinate (52.0 mg, 0.509 mmol), copper (II) trifluoromethanesulfonate (115 mg, 0.318 mmol) and N,N′-dimethylethylene diamine (0.100 mL, 0.939 mmol). The mixture is warmed at 110° C. for 35 minutes in a microwave reactor. The reaction is the diluted with saturated aqueous ammonium chloride (7 mL) and extracted with EtOAc (4×7 mL). The combined organic layers are washed with saturated aqueous ammonium chloride (3×7 mL) and brine (3×7 mL), dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0.5-3% methanol in dichloromethane. The resulting solid is triturated with dichloromethane-ether to afford the title compound.

Workup

  1. extractionextracted with EtOAc (4×7 mL)
  2. washThe combined organic layers are washed with saturated aqueous ammonium chloride (3×7 mL) and brine (3×7 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with a gradient of 0.5-3% methanol in dichloromethane
  8. customThe resulting solid is triturated with dichloromethane-ether

Sources & evidence

ORD record
ord-d7c7f033001e4acca7a8dfb56d4519bb
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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