N,N-Dimethylglycine → HCID 24953726, compound

HRID 230689Notes

Reaction equation

HRID 230689 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][S:10]2(=[O:15])=[O:14])=[CH:4][CH:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[NH:20][N:19]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[O:14]=[S:10]1(=[O:15])[CH2:11][CH2:12][CH2:13][N:9]1[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:20]2[C:21]3[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=3[C:18]([C:17]([F:16])([F:28])[F:27])=[N:19]2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 11430Potassium CarbonateHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazoleHCID 47176171950785-37-2

Product 1

HCID 24953726HCID 24953726, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 2-[(4-bromophenyl)methyl]isothiazolidine 1,1-dioxide (290 mg, 1.0 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (190 mg, 1.0 mmol), N,N-dimethylglycine (20 mol %, 21 mg, 0.2 mmol), copper (I) iodide (10 mol %, 19 mg, 0.1 mmol) and potassium carbonate (2 mmol, 276 mg) in dimethylsulfoxide (4 ml) was stirred at 190° C. in a microwave reactor for 30 minutes. The reaction mix was partitioned between dichloromethane (5 ml) and water (5 ml). The organic layer was added to a 5 g isolute silica sep-pak column and eluted with ethyl acetate. The solvent was removed under reduced pressure and the residue purified by mass directed auto-prep (MDAP) to give a greasy product which was partitioned between water and dichloromethane. The organic layer was dried over sodium sulphate and evaporated in air to give the title compound as a yellow oil (103 mg, 26%).

Workup

  1. additionThe reaction mix
  2. customwas partitioned between dichloromethane (5 ml) and water (5 ml)
  3. additionThe organic layer was added to a 5 g isolute silica sep-pak column
  4. washeluted with ethyl acetate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified by mass
  7. customto give a greasy product which
  8. customwas partitioned between water and dichloromethane
  9. dry with materialThe organic layer was dried over sodium sulphate
  10. customevaporated in air

Sources & evidence

ORD record
ord-182da43cf540491abdfb28c336cab52e
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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