HCID 178422094, compound → HCID 58936935, compound

HRID 855948Notes

Reaction equation

HRID 855948 reaction equation
[C:1]([N:3]=[C:4]([NH2:17])[NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([I:15])[CH:14]=1)[NH:11][C:10]([CH3:16])=[CH:9]2)#[N:2]>COCCOCCOC>[I:15][C:13]1[C:12]2[NH:11][C:10]([CH3:16])=[CH:9][C:8]=2[C:7]2[C:6]([CH:14]=1)=[N:5][C:4]([NH2:17])=[N:3][C:1]=2[NH2:2]

Participants

3

Reactant 1

HCID 178422094HCID 178422094, compound

Product 1

HCID 58936935HCID 58936935, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N″-cyano-N-(7-iodo-2-methyl-1H-indol-5-yl)guanidine XVIII (0.86 g, 2.54 mmol) in 2-methoxyethyl ether (20 mL) was heated to 175° C. for 28 h. The reaction mixture was cooled to 25° C. and the solid formed was removed by filtration and washed with methanol. The filtrate was concentrated in vacuo and the residue triturated with methanol and ether to give a brown solid which was isolated by filtration and dried to give 6-iodo-8-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine XIX (120 mg, 14%) as a brown solid: LRMS for C11H10IN5 (M+H)+ at m/z=340.

Workup

  1. customthe solid formed
  2. customwas removed by filtration
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue triturated with methanol and ether
  6. customto give a brown solid which
  7. customwas isolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-58cd2f803f8f46fb84f797cc9a0a127d
Source dataset
uspto-grants-2007_08
Patent number
US07262297B2

Reaction notes

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