Acetyl chloride → HCID 18399332, compound

HRID 1019382Notes

Reaction equation

HRID 1019382 reaction equation
[NH2:1][N:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:28].C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37].[C:40](OCC)(=[O:42])[CH3:41]>O1CCCC1.O>[C:36]([N:1]([C:40](=[O:42])[CH3:41])[N:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:16]2[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:28])(=[O:38])[CH3:37]

Participants

7

Reactant 4

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 18399304HCID 18399304, compound

Product 1

HCID 18399332HCID 18399332, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the compound obtained in Example 68 (200 mg) and triethylamine (145 μd) in tetrahydrofuran (15 ml) is cooled to −20° C., and thereto is added a solution of acetyl chloride (61 mg) in tetrahydrofuran (5 ml). The reaction mixture is stirred at the same temperature for one hour, and warmed to room temperature. To the reaction mixture are added acetyl chloride (122 mg) and triethylamine (290 μl), and the mixture is stirred at room temperature overnight. To the reaction mixture are added ethyl acetate and water, and the ethyl acetate layer is separated, 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-diacetylamino-3-methoxycarbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (75 mg) as listed in Table 6.

Workup

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

Sources & evidence

ORD record
ord-23be52011f5140b494c46d4109e78d7f
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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