Potassium Carbonate → HCID 18399283, compound

HRID 1019394Notes

Reaction equation

HRID 1019394 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.O[C:33]1[CH:42]=[C:41]2[C:36]([C:37]([C:54]3[CH:59]=[C:58]([O:60][CH3:61])[C:57]([O:62][CH3:63])=[C:56]([O:64][CH3:65])[CH:55]=3)=[C:38]([C:50]([O:52][CH3:53])=[O:51])[N:39]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:40]2=[O:43])=[CH:35][C:34]=1[O:66][CH3:67].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C)C=O.C(OCC)(=O)C.O>[CH3:67][O:66][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][C:33]=1[O:7][C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8])[C:40](=[O:43])[N:39]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]([C:50]([O:52][CH3:53])=[O:51])=[C:37]2[C:54]1[CH:55]=[C:56]([O:64][CH3:65])[C:57]([O:62][CH3:63])=[C:58]([O:60][CH3:61])[CH:59]=1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 12473Pyrrole-2-Carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18398823HCID 18398823, compound

Product 1

HCID 18399283HCID 18399283, compoundYield 75.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyrrol-2-carboxylic acid (38.4 mg) and 1-hydroxybenzotriazole monohydrate (53 mg) are dissolved in acetonitrile (10 ml), and thereto is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66.3 mg), and the mixture is stirred at room temperature for 30 minutes. The reaction mixture is added to a solution of the compound obtained in Example 214 (162 mg) and potassium carbonate (48 mg) in dimethylformamide (10 ml), and the mixture is stirred at room temperature for 30 minutes. Water and ethyl acetate are added to the reaction mixture. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is crystallized from diethyl ether to give 6-methoxy-3-methoxycarbonyl-2-phenyl-7-(2-pyrrolylcarbonyloxy)-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (145 mg) as listed in Table 18.

Workup

  1. stirringthe mixture is stirred at room temperature for 30 minutes
  2. customThe ethyl acetate layer is separated
  3. washwashed
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-e4612ae5ea2b4427b26a5a4a525c29da
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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