Pyridine → HCID 66638494, compound

HRID 1094979Notes

Reaction equation

HRID 1094979 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]([NH2:11])[S:9][C:8]2=[CH:12][CH:13]=[CH:14][C:7]=12)=[O:5])[CH3:2].N1C=CC=CC=1.CO[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1OC)[C:26](Cl)=[O:27].[CH2:34]([Cl:36])Cl>>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:14][CH2:13][CH2:12][C:8]=2[S:9][C:10]=1[NH:11][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[C:23]([CH2:34][Cl:36])[CH:24]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 77070Veratroyl chloride2×HCID 53438117HCID 53438117, compound2×

Product 1

HCID 66638494HCID 66638494, compound

Conditions

Temperature
0 °C

Procedure

Ethyl-2-aminocyclopenta(B)thiophene-3-carboxylate (compound A) (1.0 g) was dissolved in anhydrous methylene chloride (20.0 ml). Subsequently, pyridine (760 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (880 μl) were added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-(3-chloromethyl-benzoylamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid ethyl ester as a useful intermediate (800 mg, crude yield 100%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionthe mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated

Sources & evidence

ORD record
ord-1665d4021e31421d9892748e6d3bf880
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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