Cyanoacetic acid → HCID 71618550, compound

HRID 2201865Notes

Reaction equation

HRID 2201865 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([N:11]2[C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[CH:13]=[CH:12]2)=[O:10])=[C:4]([Cl:20])[CH:3]=1.[C:21]([CH2:23][C:24](O)=[O:25])#[N:22].OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:21]([CH2:23][C:24]([NH:1][C:2]1[CH:3]=[C:4]([Cl:20])[C:5]([C:9]([N:11]2[C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[CH:13]=[CH:12]2)=[O:10])=[C:6]([Cl:8])[CH:7]=1)=[O:25])#[N:22]

Participants

7

Reactant 5

HCID 9740Cyanoacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 86720659HCID 86720659, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 71618550HCID 71618550, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-amino-2,6-dichlorophenyl)(1H-pyrrolo[3,2-c]pyridin-1-yl)methanone (60 mg, 0.19 mmol) in dimethylformamide (1 mL) was added cyanoacetic acid (25 mg, 0.29 mmol), hydroxybenzotriazole (39.73 mg, 0.29 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (56.17 mg, 0.29 mmol) and N,N-diisopropylethyl amine (0.06 mL, 0.31 mmol) in the same order. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was poured onto water (10 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulphate, filtered and the solvent was removed under rotary evaporator. The product was purified by silica gel column chromatography using dichloromethane and methanol (1.5-2%) as eluant to yield 2-cyano-N-[3,5-dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]acetamide (8.7 mg, 12%).

Workup

  1. additionThe reaction mixture was poured onto water (10 mL)
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic layer was washed with saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customthe solvent was removed under rotary evaporator
  7. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9c9e55a22394420187bcec51e60571bf
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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