Dimethylformamide → N-[3-(5-{2-[3-pyridyl]ethenyl}fur-2-yl)-1-methyl-2-propynyl]-N-hydroxyurea

HRID 52171

反応式

HRID 52171 の反応式
I[C:2]1[O:3][C:4]([CH:7]=[CH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:6]=1.[OH:15][N:16]([CH:20]([C:22]#[CH:23])[CH3:21])[C:17]([NH2:19])=[O:18].CN(C)C=O.[NH4+].[OH-]>C(NCC)C.CC#N.CC#N.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH:8]=[CH:7][C:4]2[O:3][C:2]([C:23]#[C:22][CH:20]([N:16]([OH:15])[C:17]([NH2:19])=[O:18])[CH3:21])=[CH:6][CH:5]=2)[CH:10]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 19963264N-hydroxy-N-(butyn-2-yl)ureaHCID 545240982-Iodo-5-[2-{3-pyridyl}ethenyl]furan

生成物 1

HCID 53636693N-[3-(5-{2-[3-pyridyl]ethenyl}fur-2-yl)-1-methyl-2-propynyl]-N-hydroxyurea収率 37.9%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 6093782Bis(acetonitrile)dichloropalladium触媒HCID 8021Diethylamine溶媒

実験手順

To a stirred solution of 2-iodo-5-[2-{3-pyridyl}ethenyl]furan (1.4 g, 4.7 mmol), prepared as in step 5, and N-hydroxy-N-(butyn-2-yl)urea (0.64 g, 5 mmol), prepared as in step 2, in diethylamine (10 mL) was added dimethylformamide (1 mL), triphenylphosphine (0.026 g, 0.1 mmol), cuprous iodide (5 mg, 25 mmol) and bis(acetonitrile)palladium(II) chloride (13 mg, 50 mmol). The mixture was stirred overnight at ambient temperature. Aqueous NH4OH was added and the mixture extracted thoroughly with CH2Cl2. The combined organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel eluting with 5% MeOH--CH2Cl2 to afford an off-white solid. Recrystallization from ethyl acetate-hexanes gave 530 mg of the title compound. m.p. 166° C. 1H NMR (DMSO-d6, 300 MHz) δ1.38 (d, J=7 Hz, 3H), 5.19 (q, J=7 Hz, 1H), 6.61 (bs, 2H), 6.82 (d, J=3 Hz, 1H), 6.82 (d, J=3 Hz, 1H), 7.09 (d, J=16 Hz, 1H), 7.25 (d, J=16 Hz, 1H), 7.39 (m, 1H), 7.77 (m, 1H), 8.03 (m, 1H), 8.45 (m, 1H), 8.77 (m, 1H), 9.43 (s, 1H). MS (DCI/NH3) m/e 298 (M+H)+. Anal calcd for C16H15N3O3 : C, 64.63; H, 5.08; N, 14.13. Found: C, 64.01; H, 5.09; N, 14.06.

後処理

  1. extractionthe mixture extracted thoroughly with CH2Cl2
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel eluting with 5% MeOH
  6. customCH2Cl2 to afford an off-white solid
  7. customRecrystallization from ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-4b0f31714e074fc6b058cad5f5fa22a2
出典データセット
uspto-grants-1997_04
特許番号
US05616596

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