Water → Cyclopentanecarboxylic acid (3-cyano-5-ethyl-4,6-dimethyl-thieno[2,3-b]pyridin-2-yl)amide

HRID 1991462Notes

Reaction equation

HRID 1991462 reaction equation
[NH2:1][C:2]1[S:14][C:5]2=[N:6][C:7]([CH3:13])=[C:8]([CH2:11][CH3:12])[C:9]([CH3:10])=[C:4]2[C:3]=1[C:15]#[N:16].[CH:17]1([C:22](Cl)=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]1.O>N1C=CC=CC=1>[C:15]([C:3]1[C:4]2[C:5](=[N:6][C:7]([CH3:13])=[C:8]([CH2:11][CH3:12])[C:9]=2[CH3:10])[S:14][C:2]=1[NH:1][C:22]([CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:23])#[N:16]

Participants

5

Reactant 3

HCID 962WaterHCID 78284Cyclopentanecarbonyl chlorideHCID 11593819HCID 11593819, compound

Product 1

HCID 11522716Cyclopentanecarboxylic acid (3-cyano-5-ethyl-4,6-dimethyl-thieno[2,3-b]pyridin-2-yl)amideYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-ethyl-4,6-dimethylthieno[2,3-b]pyridine-3-carbonitrile (23 mg, 0.10 mmol) in pyridine (2.5 mL) was added cyclopentanecarbonyl chloride (15 mg, 0.11 mmol). The mixture was stirred at room temperature overnight, poured into water (10 mL) and extracted with DCM (10 mL). The organic layer was separated and washed with HCl (2 N, 2×3 mL), water (3×3 mL) and brine (3 mL), dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to provide essentially pure cyclopentanecarboxylic acid (3-cyano-5-ethyl-4,6-dimethyl-thieno[2,3-b]pyridin-2-yl)amide (28 mg, 86%).

Workup

  1. extractionextracted with DCM (10 mL)
  2. customThe organic layer was separated
  3. washwashed with HCl (2 N, 2×3 mL), water (3×3 mL) and brine (3 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6e8d7195213948c7a5e1feca925d8c7d
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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