1,2-Dichloroethane → HCID 87249480, compound

HRID 885870Notes

Reaction equation

HRID 885870 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:30])/[CH:17]=[CH:18]/[C:19]3[CH:24]=CC(/C=C/C(O)=O)=[CH:21][CH:20]=3)=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.C1C=CC2[N:39]([OH:40])N=NC=2C=1.C(Cl)C[Cl:43].NO[CH:47]1[CH2:52][CH2:51][CH2:50][CH2:49][O:48]1>C1COCC1>[ClH:43].[OH:40][NH:39][C:49](=[O:48])/[CH:50]=[CH:51]/[C:52]1[CH:47]=[CH:24][C:19](/[CH:18]=[CH:17]/[C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][CH:6]3[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]3)=[CH:11][CH:12]=2)=[O:30])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67049368HCID 67049368, compound

Product 1

HCID 87249480HCID 87249480, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-(4-{(E)-3-[4-(1-methyl-piperidin-4-ylmethyl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid hydrochloride (160 mg, 0.376) was dissolved in THF (5 ml), and then HOBT (66.5 mg, 0.493 mmol), EDC (94.6 mg, 0.493 mmol), TEA (0.171 ml, 1.233 mmol) and NH2OTHP (47.6 mg, 0.411 mmol) were added to the resulting solution. The mixture was stirred overnight at room temperature and then partitioned between water and AcOEt. The organic extracts were dried over Na2SO4 and evaporated in vacuo. The crude mixture was dissolved in DCM and treated with HCl/Et2O for 2 h. The precipitate was filtered off to give 90 mg (E)-N-hydroxy-3-(4-{(E)-3-[4-(1-methyl-piperidin-4-ylmethyl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylamide hydrochloride.

Workup

  1. custompartitioned between water and AcOEt
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. customevaporated in vacuo
  4. dissolutionThe crude mixture was dissolved in DCM
  5. additiontreated with HCl/Et2O for 2 h
  6. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-fbbe0293cf5f411a92e14178d9c987f4
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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