Guanidine Hydrochloride → HCID 86627578, compound

HRID 1970071Notes

Reaction equation

HRID 1970071 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CN(C)[CH:8]=[CH:9][C:10]([C:12]1[CH:21]=[CH:20][C:19]2[NH:18][C:17](=[O:22])[C:16]3[NH:23][CH:24]=[CH:25][C:15]=3[C:14]=2[CH:13]=1)=O.[CH2:27]([C:29]([O-:31])=[O:30])[CH3:28]>CC(N(C)C)=O>[NH2:4][C:3]1[N:5]=[C:10]([C:12]2[CH:21]=[CH:20][C:19]3[NH:18][C:17](=[O:22])[C:16]4[NH:23][CH:24]=[CH:25][C:15]=4[C:14]=3[CH:13]=2)[CH:9]=[CH:8][N:2]=1.[CH2:27]([C:29]([O-:31])=[O:30])[CH3:28]

Participants

4

Reactant 2

HCID 5742Guanidine HydrochlorideHCID 86627579HCID 86627579, compound

Product 1

HCID 86627578HCID 86627578, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

83 mg (0.87 mmol) of guanidine hydrochloride is added to a suspension of 204 mg (0.58 mmol) of 8-(3-dimethylamino-acryloyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 2.3 mL of anhydrous dimethylacetamide. The mixture is stirred at 130° C. for 4 days then the solvent is evaporated. The residue is triturated with methanol to give a solid which is collected by filtration then washed with methanol and then diisopropyl ether. After drying, 114 mg (56%) of 8-(2-amino-pyrimidin-4-yl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a brown solid.

Workup

  1. customthe solvent is evaporated
  2. customThe residue is triturated with methanol
  3. customto give a solid which
  4. filtrationis collected by filtration
  5. washthen washed with methanol
  6. customAfter drying

Sources & evidence

ORD record
ord-f4501c6337aa49aeaf88ac06cd7e379f
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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