Carbonic acid, compound with phenylguanidine (1:1) → HCID 86627580, compound

HRID 1970072Notes

Reaction equation

HRID 1970072 reaction equation
C(=O)(O)O.[C:5]1([NH:11][C:12]([NH2:14])=[NH:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CN(C)[CH:17]=[CH:18][C:19]([C:21]1[CH:30]=[CH:29][C:28]2[NH:27][C:26](=[O:31])[C:25]3[NH:32][CH:33]=[CH:34][C:24]=3[C:23]=2[CH:22]=1)=O.[CH2:36]([C:38]([O-:40])=[O:39])[CH3:37]>CC(N(C)C)=O>[O:31]=[C:26]1[C:25]2[NH:32][CH:33]=[CH:34][C:24]=2[C:23]2[CH:22]=[C:21]([C:19]3[CH:18]=[CH:17][N:14]=[C:12]([NH:11][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:13]=3)[CH:30]=[CH:29][C:28]=2[NH:27]1.[CH2:36]([C:38]([O-:40])=[O:39])[CH3:37]

Participants

4

Reactant 2

HCID 16217093Carbonic acid, compound with phenylguanidine (1:1)HCID 86627579HCID 86627579, compound

Product 1

HCID 86627580HCID 86627580, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

51 mg (0.38 mmol) of phenylguanidine carbonate is added to a suspension of 88 mg (0.25 mmol) of 8-(3-dimethylamino-acryloyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 2 mL of anhydrous dimethylacetamide. The mixture is stirred at 130° C. for 2 days then the solvent is evaporated. The residue is triturated with acetonitrile to give a solid which is collected by filtration then washed with acetonitrile then diisopropyl ether. After drying, 47 mg (44%) of 4-oxo-8-(2-phenylamino-pyrimidin-4-yl)-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 acetonitrile
  3. customto give a solid which
  4. filtrationis collected by filtration
  5. washthen washed with acetonitrile
  6. customAfter drying

Sources & evidence

ORD record
ord-d31efd623d5345759e505eeecbc2e0a7
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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