Benzenepropanoic acid → HCID 3378174, compound

HRID 2236089Notes

Reaction equation

HRID 2236089 reaction equation
[C:1]([OH:11])(=O)[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH2:23]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31]2[C:34]([C:38]#[N:39])=[C:35]([NH2:37])[S:36][C:30]=2[CH2:29]1)=[O:27])[CH3:24].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:23]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31]2[C:34]([C:38]#[N:39])=[C:35]([NH:37][C:1](=[O:11])[CH2:2][CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[S:36][C:30]=2[CH2:29]1)=[O:27])[CH3:24]

Participants

7

Reactant 5

HCID 107Benzenepropanoic acidHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2816609ethyl 2-amino-3-cyano-5,7-dihydro-4H-thieno[2,3-c]pyridine-6-carboxylate

Product 1

HCID 3378174HCID 3378174, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a sealed test tube hydrocinnamic acid (1.5 mmol) is suspended in a mixture of DMF (0.15 mmol) and dichloromethane (7.5 mL). A solution of oxalyl chloride (3.0 mmol) in dichloromethane (7.5 mL) is then added and the mixture stirred for 1 h at room temperature. After that, the solvents and excess of oxalyl chloride are removed in vacuo, the residue is dissolved in toulene (7.5 mL) and added to 2-amino-3-cyano-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid ethyl ester (1 mmol) in a vial suitable for microwave technology. Diisopropyl ethyl amine (1.5 mmol) is added, the vial is capped and the mixture heated for 30 min at 150° C. using microwave technology. Purification is achieved by filtration followed by washing (water) and crystallization (ethanol).

Workup

  1. customAfter that, the solvents and excess of oxalyl chloride are removed in vacuo
  2. dissolutionthe residue is dissolved in toulene (7.5 mL)
  3. customthe vial is capped
  4. temperaturethe mixture heated for 30 min at 150° C.
  5. customPurification
  6. filtrationis achieved by filtration
  7. washby washing
  8. custom(water) and crystallization (ethanol)

Sources & evidence

ORD record
ord-dfa9776e487c449493c81b42c7892b7a
Source dataset
uspto-grants-2010_05
Patent number
US07714135B2

Reaction notes

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