HCID 54160924, compound → HCID 18399114, compound

HRID 1019372Notes

Reaction equation

HRID 1019372 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:38]3[CH:43]=[C:42]([O:44][CH3:45])[C:41]([O:46][CH3:47])=[C:40]([O:48][CH3:49])[CH:39]=3)=[C:14]([C:34]([O:36][CH3:37])=[O:35])[N:15]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:22][CH:21]=3)[C:16]2=[O:19])=[CH:11][C:10]=1[O:50][CH3:51])C1C=CC=CC=1>O1CCCC1.CO.[C].[Pd]>[C:30]([O:29][C:27]([NH:26][C:23]1[CH:24]=[CH:25][C:20]([N:15]2[C:14]([C:34]([O:36][CH3:37])=[O:35])=[C:13]([C:38]3[CH:43]=[C:42]([O:44][CH3:45])[C:41]([O:46][CH3:47])=[C:40]([O:48][CH3:49])[CH:39]=3)[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:50][CH3:51])[CH:11]=3)[C:16]2=[O:19])=[CH:21][CH:22]=1)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 1

HCID 54160924HCID 54160924, compound

Product 1

HCID 18399114HCID 18399114, compoundYield 89.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in Example 4 (17.0 g) in a mixture of tetrahydrofuran (150 ml) and methanol (100 ml) is added palladium-carbon (1.0 g) under nitrogen atmosphere, and the mixture is subjected to catalytic reduction (3 atms) for one hour. The palladium-carbon is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is crystallized from diethyl ether to give 2-[4-(tert-butoxycarbonylamino)phenyl]-7-hydroxy-6-methoxy-3-methoxycarbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (13.3 g) as listed in Table 2.

Workup

  1. customThe palladium-carbon is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-b1d2c1a94d494265b0177a54b78f553c
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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