HCID 178512364, compound → HCID 178508676, compound

HRID 1765025Notes

Reaction equation

HRID 1765025 reaction equation
[C:1]([N:3]=[C:4]([NH2:16])[NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([I:15])[CH:14]=1)[NH:11][CH:10]=[CH:9]2)#[N:2]>COCCOCCOC.CO>[I:15][C:13]1[C:12]2[NH:11][CH:10]=[CH:9][C:8]=2[C:7]2[C:6]([CH:14]=1)=[N:5][C:4]([NH2:16])=[N:3][C:1]=2[NH2:2]

Participants

4

Reactant 1

HCID 178512364HCID 178512364, compound

Product 1

HCID 178508676HCID 178508676, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8150DiglymeSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N″-cyano-N-(7-iodo-1H-indol-5-yl)guanidine V (6.08 g, 18.7 mmol) in 2-methoxyethyl ether (50 mL) was heated to 175° C. for 32.5 h. The reaction mixture was cooled to 25° C., the resulting solids removed by filtration and washed with methanol. The filtrate was concentrated in vacuo to give a brown oil. The residue was dissolved in methanol and then absorbed onto Merck Silica gel 60, 230–400 mesh (25 g). Flash chromatography (Merck Silica gel 60, 230–400 mesh, 90/10/1 methylene chloride/methanol/ammonium hydroxide) afforded 6-iodo-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine VI (3.61 g, 59%) as a brown solid: 1H NMR (DMSO-d6, 300 MHz) δ 11.36 (broad s, 1H), 7.45 (broad s, 1H), 7.43 (t, J=2.93 Hz, 1H), 7.20 (s, 1H), 6.74 (broad s, 2H), 5.78 (broad s, 2H).

Workup

  1. customthe resulting solids removed by filtration
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a brown oil
  5. customabsorbed onto Merck Silica gel 60, 230–400 mesh (25 g)

Sources & evidence

ORD record
ord-e14d451031054105a047a4bab84d239b
Source dataset
uspto-grants-2007_06
Patent number
US07226915B2

Reaction notes

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