Acrylic Acid → HCID 10161003, compound

HRID 2213782Notes

Reaction equation

HRID 2213782 reaction equation
[NH2:1][C:2]1[C:7]2[S:8][C:9]3[C:10](=[N:11][CH:12]=[C:13]([C:23]#[N:24])[C:14]=3[NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:25](O)(=[O:28])[CH:26]=[CH2:27].C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>O1CCCC1.CN(C)C=O>[Br:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[NH:15][C:14]1[C:13]([C:23]#[N:24])=[CH:12][N:11]=[C:10]2[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH:1][C:25](=[O:28])[CH:26]=[CH2:27])[C:7]=3[S:8][C:9]=12

Participants

7

Reactant 4

HCID 6581Acrylic AcidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219564126-Amino-4-(3-bromoanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrile

Product 1

HCID 10161003HCID 10161003, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 0.138 g (0.349 mM) portion of 6-amino-4-(3-bromoanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrile is dissolved in 2 mL of tetrahydrofuran and 2 mL of dimethylformamide at 0° C. To this is added 0.042 g (0.583 mM) of acrylic acid, 0.105 g (0.575 mM) of N,N-diisopropylethylamine and 0.106 g (0.554 mM) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride with stirring under nitrogen. The reaction mixture is stirred for 48 hours at room temperature, and the solvent is removed under reduced pressure. The residue is worked up with water (3 mL) and extracted with methylene chloride (10 mL), dried with sodium sulfate and evaporated. Purification of the product is carried out by silica get chromatography, eluting with 20:1 chloroform/methanol. Further purification is achieved by preparative thin layer chromatography, eluting with the same solvent system. Finally, the product is washed with ether to provide 0.068 g (43%) of N-[4-(3-bromoanilino)-3-cyano[1]benzothieno[3,2-b]pyridin-6-yl]acrylamide, m.p. 286–287° C.

Workup

  1. customat 0° C
  2. stirringThe reaction mixture is stirred for 48 hours at room temperature
  3. customthe solvent is removed under reduced pressure
  4. extractionextracted with methylene chloride (10 mL)
  5. dry with materialdried with sodium sulfate
  6. customevaporated
  7. customPurification of the product
  8. customget chromatography
  9. washeluting with 20:1 chloroform/methanol
  10. customFurther purification
  11. washeluting with the same solvent system
  12. washFinally, the product is washed with ether

Sources & evidence

ORD record
ord-8786c5dd167640fda34c371e57a8cfcf
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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