Morpholine → HCID 70137744, compound

HRID 1019390Notes

Reaction equation

HRID 1019390 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.[NH:57]1[CH2:62][CH2:61][O:60][CH2:59][CH2:58]1>CN(C)C=O.C(OCC)(=O)C.O>[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]([CH:59]1[O:60][CH2:61][CH2:62][NH:57][CH2:58]1)=[O:2])=[C:13]2[C:14]1[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 18398798HCID 18398798, compound

Product 1

HCID 70137744HCID 70137744, compoundYield 51.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound obtained in Example 128 (1.50 g), 1,3-dicyclohexylcarbodiimide (793 mg) and 1-hydroxybenzotriazole (588 mg) in dimethylformamide (30 ml) is stirred at room temperature for one hour, and thereto is added morpholine (335 mg), and the mixture is stirred for two hours. The mixture is further stirred at 50° C. for four 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 crystallized from diethyl ether-ethyl acetate to give 6,7-dimethoxy-2-methyl-3-morphlino-carbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (893 mg) as listed in Table 12.

Workup

  1. stirringThe mixture is further stirred at 50° C. for four hours
  2. customThe ethyl acetate layer is separated
  3. washwashed
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is crystallized from diethyl ether-ethyl acetate

Sources & evidence

ORD record
ord-f4e67ecb317d45979cfd13678b8cd6c4
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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