N-Hydroxyethylisonicotinamide → HCID 57664412, compound

HRID 656664Notes

Reaction equation

HRID 656664 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:23]1([NH:26][C:27]([C:29]2[S:42][C:32]3=[N:33][C:34](S(C)=O)=[C:35]([Cl:38])[C:36]([CH3:37])=[C:31]3[C:30]=2[NH2:43])=[O:28])[CH2:25][CH2:24]1>C1COCC1>[CH:23]1([NH:26][C:27]([C:29]2[S:42][C:32]3=[N:33][C:34]([O:1][CH2:2][CH2:3][NH:4][C:5]([C:6]4[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=4)=[O:12])=[C:35]([Cl:38])[C:36]([CH3:37])=[C:31]3[C:30]=2[NH2:43])=[O:28])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 73327N-HydroxyethylisonicotinamideHCID 2733832Lithium HexamethyldisilazideHCID 576644203-Amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

Product 1

HCID 57664412HCID 57664412, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(2-hydroxyethyl)-isonicotinamide (0.831 g, 5.00 mmol) in THF (2.5 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl) amide (1.0 M in hexanes)(2.50 ml, 2.50 mmol). The reaction mixture is stirred for 15 minutes and then is treated with 3-amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (0.345 g, 1.00 mmol). The reaction mixture is heated at 80° C. in a sealed tube for 2 hours, cooled to room temperature, and then quenched by the addition of water (15 ml). The mixture is diluted to 100 ml with water and then cooled to 0° C. and stirred. A yellow precipitate is formed. This solid is collected by filtration, slurried in EtOAc, and filtered again to give a yellow solid which is placed in the vacuum oven to dry (50° C. for 3 hours). This affords the title compound as a yellow solid (0.046 g, 10%). Mass (m/z): 446.3 (M++1), 444.2 (M+−1).

Workup

  1. temperaturecooled to room temperature
  2. customquenched by the addition of water (15 ml)
  3. additionThe mixture is diluted to 100 ml with water
  4. temperaturecooled to 0° C.
  5. stirringstirred
  6. customA yellow precipitate is formed
  7. filtrationThis solid is collected by filtration
  8. filtrationfiltered again
  9. customto give a yellow solid which
  10. customto dry (50° C. for 3 hours)

Sources & evidence

ORD record
ord-ac538e73f5d14168a346866a81ac8165
Source dataset
uspto-grants-2011_12
Patent number
US08071776B2

Reaction notes

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