Acrylic Acid → HCID 10161003, compound

HRID 989337Notes

Reaction equation

HRID 989337 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 0C. 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 gel 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. stirringThe reaction mixture is stirred for 48 hours at room temperature
  2. customthe solvent is removed under reduced pressure
  3. extractionextracted with methylene chloride (10 mL)
  4. dry with materialdried with sodium sulfate
  5. customevaporated
  6. customPurification of the product
  7. washeluting with 20:1 chloroform/methanol
  8. customFurther purification
  9. washeluting with the same solvent system
  10. washFinally, the product is washed with ether

Sources & evidence

ORD record
ord-50ebd6b0dbb74af0ba0e5c36dc2027ee
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

Loading…