HCID 10870074, compound → HCID 11759373, compound

HRID 1793120Notes

Reaction equation

HRID 1793120 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:6]=[C:7](I)[NH:8][C:9]=1[CH2:10][CH2:11][CH3:12])=[O:4]>CO>[CH3:1][NH:2][C:3]([C:5]1[N:6]=[C:7]([C:7]2[NH:8][C:9]([CH2:10][CH2:11][CH3:12])=[C:5]([C:3]([NH:2][CH3:1])=[O:4])[N:6]=2)[NH:8][C:9]=1[CH2:10][CH2:11][CH3:12])=[O:4]

Participants

3

Reactant 1

HCID 10870074HCID 10870074, compound

Product 1

HCID 11759373HCID 11759373, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodide 6a (0.35 g; 1.2 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was dissolved in CH2Cl2. Upon standing, a white solid precipitated. This material was collected by filtration and was washed with ice-cold CH2Cl2 to afford 0.080 g (43%) of 1a. mp>260 ÿC; TLC (EtOAc): Rf=0.32; 1H NMR (DMSO-d6): δ 0.83 (t, 6H), 1.61 (m, 4H), 2.73 (d, 6H), 2.89 (t, 4H), 7.50 (br t, 2H); 13C NMR (DMSO-d6): δ 13.1, 21.9, 24.7, 30.2, 130.3, 135.6, 163.0; UV/vis (CH3OH): λmax (ε M−1cm−1)=286 (18500), 294 (18200), 309 (9860); Anal. calcd for C16H24N6O2.0.25(CH2Cl2): C, 55.19; H, 6.98; N, 23.76; found: C, 54.93; H, 6.71; N, 23.74.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under vacuum
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. customa white solid precipitated
  5. filtrationThis material was collected by filtration
  6. washwas washed with ice-cold CH2Cl2

Sources & evidence

ORD record
ord-c5c47ba74d2c4e2f8477997e73d47b11
Source dataset
uspto-grants-2006_07
Patent number
US07078528B2

Reaction notes

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