Morpholine → HCID 53817948, compound

HRID 1019376Notes

Reaction equation

HRID 1019376 reaction equation
[Na].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:37])=[CH:7][CH:6]=1)(O)=[O:3].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH:60]1[CH2:65][CH2:64][O:63][CH2:62][CH2:61]1>C(Cl)Cl.C(OCC)(=O)C.O>[CH3:24][O:23][C:21]([C:20]1[N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:2]([N:60]3[CH2:65][CH2:64][O:63][CH2:62][CH2:61]3)=[O:3])=[CH:6][CH:7]=2)[C:12](=[O:37])[C:13]2[C:18]([C:19]=1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:22]

Participants

8

Reactant 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70152632HCID 70152632, compound

Product 1

HCID 53817948HCID 53817948, compoundYield 96.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound obtained in Example 21 (200 mg), 1-hydroxybenzotriazole (69 mg) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (86 mg) in methylene chloride (10 ml) is stirred at room temperature for 30 minutes. To the mixture is added a solution of morpholine (71 mg) in methylene chloride (2 ml), and the mixture is stirred at room temperature overnight. After the reaction is complete, to the 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 to give 3-methoxycarbonyl-2-[4-(morpholinocabonyl) phenyl]-4-(3,4,5-trimethoxyphenyl)-1(2H) isoquinolinone (210 mg) as listed in Table 4.

Workup

  1. customThe ethyl acetate layer is separated
  2. washwashed
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-ac0b1aa6c7804a38b9dca52819b178ef
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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