1,2-Dichloroethane → HCID 24756798, compound

HRID 885868Notes

Reaction equation

HRID 885868 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:31])/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28](O)=[O:29])=[CH:22][CH:21]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])[NH2:3].C1C=CC2[N:40]([OH:41])N=NC=2C=1.C(Cl)CCl.NOC1CCCCO1>CN(C=O)C>[OH:41][NH:40][C:28](/[CH:27]=[CH:26]/[C:23]1[CH:24]=[CH:25][C:20](/[CH:19]=[CH:18]/[C:17]([C:14]2[CH:15]=[CH:16][C:11]([N:8]3[CH2:9][CH2:10][N:5]([C:2]([NH2:3])=[O:4])[CH2:6][CH2:7]3)=[CH:12][CH:13]=2)=[O:31])=[CH:21][CH:22]=1)=[O:29]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67049685HCID 67049685, compound

Product 1

HCID 24756798HCID 24756798, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-3-(4-{(E)-3-[4-(4-Carbamoyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid hydrochloride (316 mg, 0.716 mmol) was suspended in DMF (5 ml). HOBT (193 mg, 1.43 mmol), EDC (273 mg, 1.43 mmol), TEA (0.200 ml, 1.43 mmol) and NH2OTHP (100 mg, 0.86 mmol) were added. The mixture was stirred at room temperature for 72 h and then partitioned between water and hot AcOEt. The organic extract was dried over Na2SO4, evaporated in vacuo and the crude product was crystallized from DCM/Et2O. The resulting solid was suspended in DCM and treated with HCl/Et2O for 1 h. The precipitate was filtered off, giving 103 mg of 4-(4-{(E)-3-[4-((E)-2-hydroxycarbamoyl-vinyl)-phenyl]-acryloyl}-phenyl)-piperazine-1-carboxylic acid amide as its hydrochloride salt.

Workup

  1. custompartitioned between water and hot AcOEt
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated in vacuo
  5. customthe crude product was crystallized from DCM/Et2O
  6. additiontreated with HCl/Et2O for 1 h
  7. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-cacd2c1b1daa4051b97d6a4b709dec4c
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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