1,2-Dichloroethane → HCID 59312561, compound

HRID 885830Notes

Reaction equation

HRID 885830 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:36])/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33](O)=[O:34])=[CH:27][CH:26]=3)=[CH:18][CH:17]=2)[CH2:11][CH2:10]1.C1C=CC2[N:45]([OH:46])N=NC=2C=1.C(Cl)CCl.NOC1CCCCO1.Cl.CCOCC>C1COCC1.CN(C=O)C.C(Cl)Cl>[OH:46][NH:45][C:33](=[O:34])/[CH:32]=[CH:31]/[C:28]1[CH:29]=[CH:30][C:25](/[CH:24]=[CH:23]/[C:22]([C:19]2[CH:18]=[CH:17][C:16]([NH:15][CH:12]3[CH2:11][CH2:10][N:9]([CH3:8])[CH2:14][CH2:13]3)=[CH:21][CH:20]=2)=[O:36])=[CH:26][CH:27]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 10953452Ether hydrochlorideHCID 67049881HCID 67049881, compound

Product 1

HCID 59312561HCID 59312561, compoundYield 64.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-3-(4-{(E)-3-[4-(1-methyl-piperidin-4-ylamino)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid trifluoroacetate (126 mg, 0.25 mmol), HOBT (40 mg, 0.30 mmol), EDC (58 mg, 0.30 mmol), TEA (0.10 ml, 0.75 mmol) and NH2OTHP (30 mg, 0.25 mmol) in THF (5 ml) and DMF (1 ml), was stirred at room temperature overnight and then partitioned between water and AcOEt. The organic extract was dried over Na2SO4 and evaporated in vacuo. The crude product was triturated in CH3CN/MeOH 9:1 and filtered to give a brown powder that was dissolved in DCM and treated with HCl/Et2O for 2 h. The precipitate was filtered off to give 65 mg of (E)-N-hydroxy-3-(4-{(E)-3-[4-(1-methyl-piperidin-4-ylamino)-phenyl]-3-oxo-propenyl}-phenyl)-acrylamide as its hydrochloride salt.

Workup

  1. custompartitioned between water and AcOEt
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was triturated in CH3CN/MeOH 9:1
  6. filtrationfiltered
  7. customto give a brown powder that
  8. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-de6d69b25283498ebe022a39843d52e0
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

Loading…