Water → HCID 18399126, compound

HRID 1019379Notes

Reaction equation

HRID 1019379 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]1[C:18]([C:19]([OH:21])=[O:20])=[C:17]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:35]N(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC.O>C(Cl)Cl.CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][N:9]1[C:18]([C:19]([O:21][CH3:35])=[O:20])=[C:17]([C:22]2[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 218852-Dimethylaminopyridine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 18399390HCID 18399390, compound

Product 1

HCID 18399126HCID 18399126, compoundYield 424.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound obtained in Example 66 (1.0 g), dimethylaminopyridine (26 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (448 mg) are dissolved in a mixture of methylene chloride (20 ml) and methanol (340 ml). The mixture is stirred at room temperature for 10 minutes, and thereto are added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (41 mg) and dimethylaminopyridine (26 mg), and the mixture is stirred at room temperature overnight. To the reaction mixture are added water and ethyl acetate, and the ethyl acetate layer is washed, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1) to give 2-(tert-butoxycarbonylamino)-3-methoxycarbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (438 mg) as listed in Table 6.

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. washthe ethyl acetate layer is washed
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5f8062bbe4bc46729ed3747f4051aa6b
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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