Triethylamine → HCID 18399379, compound

HRID 1019396Notes

Reaction equation

HRID 1019396 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[C:22]3[C:17](=[CH:18][C:19]([OH:43])=[C:20]([O:41][CH3:42])[CH:21]=3)[C:16]2=[O:44])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N([CH2:50][CH3:51])CC)C.[C:52](=[O:55])([O-])O.[Na+]>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:52]([O:43][C:19]1[CH:18]=[C:17]2[C:22]([C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)=[C:24]([C:25]([O:27][CH3:28])=[O:26])[N:15]([C:12]3[CH:13]=[CH:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:10][CH:11]=3)[C:16]2=[O:44])=[CH:21][C:20]=1[O:41][CH3:42])(=[O:55])[C:51]1[CH:50]=[CH:11][CH:10]=[CH:9][CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 18399114HCID 18399114, compound

Product 1

HCID 18399379HCID 18399379, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The compound obtained in Example 5 (200 mg) is dissolved in dimethylformamide (10 ml), and thereto are added benzochloride (40 μl), triethylamine (48 μl) and 4-dimethylaminopyridine (5 mg), and the mixture is stirred at room temperature overnight. After the reaction is complete, to the mixture is added a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with ethyl acetate. The extract is washed, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=1:1) to give 7-benzoyloxy-2-[4-(tert-butoxycarbonylamino)phenyl]-6-methoxy-3-methoxycarbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone as listed in Table 20.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-98b7711b4aaa4eb5a839b6993f194fa2
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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