Carbodiimide → HCID 11566479, compound

HRID 1991457Notes

Reaction equation

HRID 1991457 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:14])=[C:8]([CH2:12][CH3:13])[C:9]=2[CH3:11])[S:4][C:3]=1[C:15]([OH:17])=O.N=C=N.[C:21]1([C:27]2NN=[N:29][N:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClC(Cl)C.CN(C=O)C>[CH2:12]([C:8]1[C:9]([CH3:11])=[C:10]2[C:2]([NH2:1])=[C:3]([C:15]3[O:17][C:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:28][N:29]=3)[S:4][C:5]2=[N:6][C:7]=1[CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 160435CarbodiimideHCID 797021HCID 797021, compoundHCID 178418369HCID 178418369, compound

Product 1

HCID 11566479HCID 11566479, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-amino-5-ethyl-4,6-dimethyl-thieno[2,3-b]pyridine-2-carboxylic acid (0.16 g, 0.63 mmol) in a mixture of dichloroethane (8 mL) and DMF (2 mL) was added PS-carbodiimide (1.0 g, 1.26 mmol). The mixture was shaken for 15 min at room temperature, followed by the addition of 5-phenyltetrazole (0.042 g, 0.32 mmol). Then, the mixture was shaken at 80° C. overnight. The resin was then removed by filtration and washed with hot chloroform (2×5 mL). The filtrate was evaporated in vacuum to dryness and purified by chromatography (silica gel, dichloromethane/ethyl acetate, 9/1) to furnish the product 5-ethyl-4,6-dimethyl-2-(5-phenyl-[1,3,4]oxadiazol-2-yl)-thieno[2,3-b]pyridin-3-yl amine (0.063 g, 56%).

Workup

  1. stirringThen, the mixture was shaken at 80° C. overnight
  2. customThe resin was then removed by filtration
  3. washwashed with hot chloroform (2×5 mL)
  4. customThe filtrate was evaporated in vacuum to dryness
  5. custompurified by chromatography (silica gel, dichloromethane/ethyl acetate, 9/1)

Sources & evidence

ORD record
ord-cca7efb335ab45d5b5b8279cfcf8c932
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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