Sodium Hydroxide → HCID 178504829, compound

HRID 931272Notes

Reaction equation

HRID 931272 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[NH:29][C:11]3=[N:12][C:13]([N:16]4[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:23])[CH2:17]4)=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[N:6][CH:7]=1.[CH3:30][S:31]([O-:33])=[O:32].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>CS(C)=O.[Cu](I)I>[CH3:30][S:31]([C:2]1[CH:3]=[C:4]([C:8]2[NH:29][C:11]3=[N:12][C:13]([N:16]4[CH2:21][CH2:20][CH2:19][C@@H:18]([C:22]([N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:23])[CH2:17]4)=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[N:6][CH:7]=1)(=[O:33])=[O:32]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 178519692HCID 178519692, compound

Product 1

HCID 178504829HCID 178504829, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of R)-(1-(2-(5-bromopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (0.05 g, 0.1 mmol) in dimethylsulfoxide was added sodium methylsulfinate (NaSO2Me) (13 mg, 0.13 mmol), copper iodide, L-proline and sodium hydroxide. The reaction mixture was heated to 90° C. for 14 h. The reaction mixture was partitioned between water and ethyl acetate. The organics were concentrated under reduced pressure and the resulting crude was purified via preparative TLC to afford the title compound (25 mg, 45%). MS (ES+APCI) (M+H) 455.0; LCMS retention time: 3.859 min (Method I).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. concentrationThe organics were concentrated under reduced pressure
  3. customthe resulting crude was purified via preparative TLC

Sources & evidence

ORD record
ord-fbd393066568414e9ab61dca5064450b
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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