1,2-Dichloroethane → HCID 86641366, compound

HRID 885840Notes

Reaction equation

HRID 885840 reaction equation
[CH2:1]([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]([OH:30])=O)=[CH:22][CH:21]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3].[K].[NH2:33][O:34]C1CCCCO1.C(Cl)C[Cl:43].C1C=CC2N(O)N=NC=2C=1>C1COCC1.CN(C=O)C.O>[ClH:43].[OH:34][NH:33][C:28](=[O:30])/[CH:27]=[CH:26]/[C:23]1[CH:22]=[CH:21][C:20](/[CH:19]=[CH:18]/[C:17]([C:14]2[CH:13]=[CH:12][C:11]([N:8]3[CH2:9][CH2:10][N:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[CH2:6][CH2:7]3)=[CH:16][CH:15]=2)=[O:31])=[CH:25][CH:24]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 5462222PotassiumHCID 67049502HCID 67049502, compound

Product 1

HCID 86641366HCID 86641366, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-3-(4-{(E)-3-[4-(4-isobutyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid as potassium salt (450 mg, 1 mmol), NH2OTHP (117 mg, 1 mmol), EDC (230 mg, 1.2 mmol), HOBT (160 mg, 1.2 mmol) and TEA (0.420 ml, 3 mmol) in THF (5 ml) and DMF (5 ml) was stirred for 24 hours at room temperature. The mixture was then diluted with water and extracted with AcOEt. The organic phase was washed with water, then with a saturated NaCl solution, dried over Na2SO4 and evaporated in vacuo to dryness. The crude product was purified by flash chromatography (DCM:MeOH:NH3 98:2:0.2). The product was then dissolved in DCM and a few drops of HCl in ether were added. The mixture was stirred for 12 hours at room temperature. The precipitate was then filtered and ground in acetonitrile to obtain 300 mg of (E)-N-hydroxy-3-(4-{(E)-3-[4-(4-isobutyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylamide hydrochloride.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic phase was washed with water
  3. dry with materialwith a saturated NaCl solution, dried over Na2SO4
  4. customevaporated in vacuo to dryness
  5. customThe crude product was purified by flash chromatography (DCM:MeOH:NH3 98:2:0.2)
  6. dissolutionThe product was then dissolved in DCM
  7. additiona few drops of HCl in ether were added
  8. stirringThe mixture was stirred for 12 hours at room temperature
  9. filtrationThe precipitate was then filtered

Sources & evidence

ORD record
ord-c12834dd682b47de8d2d73cec2352cab
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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