1,2-Dichloroethane → HCID 24757064, compound

HRID 885872Notes

Reaction equation

HRID 885872 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:22](=[O:36])/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]([OH:35])=O)=[CH:27][CH:26]=2)[CH:12]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:14]=1.C1C=CC2[N:45]([OH:46])N=NC=2C=1.C(Cl)CCl.NOC1CCCCO1>C1COCC1>[Cl:8][C:9]1[CH:10]=[C:11]([C:22](=[O:36])/[CH:23]=[CH:24]/[C:25]2[CH:26]=[CH:27][C:28](/[CH:31]=[CH:32]/[C:33]([NH:45][OH:46])=[O:35])=[CH:29][CH:30]=2)[CH:12]=[C:13]([N:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)[CH:14]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67049595HCID 67049595, compound

Product 1

HCID 24757064HCID 24757064, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-(4-{(E)-3-[3-Chloro-5-(4-methyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid trifluoroacetate (40 mg, 0.076 mmol) was suspended in THF (5 ml). HOBT (16 mg, 0.116 mmol), EDC (22.3 mg, 0.116 mmol), TEA (0.04 ml, 0.291 mmol) and NH2OTHP (12 mg, 0.097 mmol) were added to the resulting mixture. The reaction was stirred at room temperature overnight and then partitioned between water and AcOEt. The organic phase was dried over Na2SO4, evaporated in vacuo and the crude product was purified by column chromatography (eluent: AcOEt/MeOH 9:1). The collected fractions were evaporated and the resulting product was dissolved in DCM and treated with HCl/Et2O for 1 h. The precipitate was filtered and purified by preparative LC-MS to give 20 mg of (E)-3-(4-{(E)-3-[3-Chloro-5-(4-methyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-N-hydroxy-acrylamide as its trifluoroacetate salt.

Workup

  1. custompartitioned between water and AcOEt
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customthe crude product was purified by column chromatography (eluent: AcOEt/MeOH 9:1)
  5. customThe collected fractions were evaporated
  6. dissolutionthe resulting product was dissolved in DCM
  7. additiontreated with HCl/Et2O for 1 h
  8. filtrationThe precipitate was filtered
  9. custompurified by preparative LC-MS

Sources & evidence

ORD record
ord-3aa77f40927c4bbf921597a5393d0780
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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