1,2-Dichloroethane → HCID 86641371, compound

HRID 885866Notes

Reaction equation

HRID 885866 reaction equation
[K+].[CH3:2][S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:32])/[CH:19]=[CH:20]/[C:21]3[CH:26]=[CH:25][C:24](/[CH:27]=[CH:28]/[C:29]([O-:31])=O)=[CH:23][CH:22]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4].C1C=CC2[N:41]([OH:42])N=NC=2C=1.C(Cl)C[Cl:45].NOC1CCCCO1>C1COCC1.CN(C=O)C>[ClH:45].[OH:42][NH:41][C:29](=[O:31])/[CH:28]=[CH:27]/[C:24]1[CH:25]=[CH:26][C:21](/[CH:20]=[CH:19]/[C:18]([C:15]2[CH:14]=[CH:13][C:12]([N:9]3[CH2:10][CH2:11][N:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH2:7][CH2:8]3)=[CH:17][CH:16]=2)=[O:32])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67049777HCID 67049777, compound

Product 1

HCID 86641371HCID 86641371, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-(4-{(E)-3-[4-(4-Methanesulfonyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid potassium salt (190 mg, 0.398 mmol) was dissolved in THF (5 ml), DMF (5 ml) and TEA (0.111 ml, 0.796 mmol). HOBT (107.4 mg, 0.796 mmol), EDC (152 mg, 0.796 mmol) and NH2OTHP (56 mg, 0.477 mmol) were added to the resulting solution. The mixture was stirred overnight at room temperature and then partitioned between water and AcOEt. The organic phase was dried over Na2SO4 and evaporated in vacuo. The crude mixture was purified by silica gel chromatography (eluent: DCM/MeOH 98:2). The resulting product was dissolved in DCM and treated with HCl/Et2O for 2 h. The precipitate was filtered and washed with DCM to give 20 mg of (E)-N-hydroxy-3-(4-{(E)-3-[4-(4-methanesulfonyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylamide hydrochloride.

Workup

  1. custompartitioned between water and AcOEt
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe crude mixture was purified by silica gel chromatography (eluent: DCM/MeOH 98:2)
  5. dissolutionThe resulting product was dissolved in DCM
  6. additiontreated with HCl/Et2O for 2 h
  7. filtrationThe precipitate was filtered
  8. washwashed with DCM

Sources & evidence

ORD record
ord-0e347bf6275a4dbb92a62594e15d4870
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

Loading…