Triethylamine → HCID 18399297, compound

HRID 1019393Notes

Reaction equation

HRID 1019393 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=3)[C:15](=[O:26])[N:14]([CH2:27][CH2:28][CH2:29][OH:30])[C:13]=2[C:31]([O:33][CH3:34])=[O:32])[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=1.C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=3)[C:15](=[O:26])[N:14]([CH2:27][CH2:28][CH2:29][O:30][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=3)[C:13]=2[C:31]([O:33][CH3:34])=[O:32])[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 82604Nicotinoyl chloride2×HCID 18399017HCID 18399017, compound

Product 1

HCID 18399297HCID 18399297, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Example 184 (190 mg) in dimethylformamide (3 ml) are added nicotinoyl chloride (69 mg) and triethylamine (0.11 ml), and the mixture is stirred at room temperature overnight To the reaction mixture are added nicotinoyl chloride (69 mg) and triethylamine (0.11 ml), and the mixture is stirred overnight. After the reaction is complete, to the mixture are added ethyl acetate and water. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure to give 4-(3-bromo-4,5-dimethoxyphenyl)-6,7-dimethoxy-3-methoxycarbonyl-2-[3-(nicotinoyloxy)propyl]-1(2H)-isoquinolinone (170 mg) as listed in Table 16.

Workup

  1. stirringthe mixture is stirred overnight
  2. customThe ethyl acetate layer is separated
  3. washwashed
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9da0c19cde044c1f90cdbae59bfec8c5
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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