Dicyclohexylcarbodiimide → HCID 178486401, compound

HRID 1019391Notes

Reaction equation

HRID 1019391 reaction equation
[C:1]([C:4]1[N:5]([CH3:31])[C:6](=[O:30])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)=[CH:11][C:10]([O:26][CH3:27])=[C:9]([O:28][CH3:29])[CH:8]=2)(O)=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[NH2:57][CH2:58][CH2:59][C:60]1[N:61]=[CH:62][NH:63][CH:64]=1>C(OCC)(=O)C.O.C(N(CC)CC)C.CN(C)C=O.C(Cl)Cl>[CH3:27][O:26][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:28][CH3:29])[C:6](=[O:30])[N:5]([CH3:31])[C:4]([C:1]([NH:57][CH2:58][CH2:59][C:60]1[N:61]=[CH:62][NH:63][CH:64]=1)=[O:2])=[C:13]2[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1

Participants

10

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 18398798HCID 18398798, compoundHCID 178419017HCID 178419017, compound

Product 1

HCID 178486401HCID 178486401, compoundYield 49.5%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methylene chloride (10 ml) and dimethylformamide (5 ml) are added the compound obtained in Example 128 (1.66 g), 1,3-dicyclohexyl carbodiimide (960 mg) and 1-hydroxybenzotriazole (710 mg), and the mixture is stirred at room temperature for 30 minutes. To the reaction mixture is added a solution of 4-(2-aminoethyl)imidazole (850 mg) and triethylamine (1.28 ml) in dimethylfomamide (5 ml), and the mixture is stirred for three hours, and then further stirred at 50° C. for 7 hours. To the reaction mixture are added water and ethyl acetate. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform:hexane=30:1) to give 6,7-dimethoxy-3-[2-(4-imidazolyl)ethylaminocarbonyl]-2-methyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (1.0 g) as listed in Table 12.

Workup

  1. stirringthe mixture is stirred for three hours
  2. stirringfurther stirred at 50° C. for 7 hours
  3. customThe ethyl acetate layer is separated
  4. washwashed
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:hexane=30:1)

Sources & evidence

ORD record
ord-eb6bd104b6d94a29a892a234a963667e
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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