Formic Acid → HCID 18399233, compound

HRID 1019392Notes

Reaction equation

HRID 1019392 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:13]=[C:14]([N:18]2[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([C:32]3[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([Br:42])[CH:33]=3)[C:25]3[C:20](=[CH:21][C:22]([O:45][CH3:46])=[C:23]([O:43][CH3:44])[CH:24]=3)[C:19]2=[O:47])[CH:15]=[CH:16][CH:17]=1.O>C(OCC)(=O)C>[CH3:44][O:43][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[O:45][CH3:46])[C:19](=[O:47])[N:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][CH:1]=[O:2])[CH:13]=1)[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]2[C:32]1[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([Br:42])[CH:33]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 18398907HCID 18398907, compound

Product 1

HCID 18399233HCID 18399233, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To formic acid (3 ml) is added acetic anhydride (3 ml), and the mixture is stirred at room temperature for four hours. To the reaction mixture is added the compound obtained in Example 176 (500 mg), and the mixture is stirred at room temperature overnight. The mixture is further stirred at 60° C. overnight. After the reaction is complete, to the reaction mixture are added water and ethyl acetate. The ethyl acetate layer is separated, washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform:acetone=10:1) to give 6,7-dimethoxy-2-[3-(formylamino)phenyl]-4-(3-bromo-4,5-dimethoxyphenyl)-3-methoxycarbonyl-1(2H)-isoquinolinone as listed in Table 16.

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. stirringThe mixture is further stirred at 60° C. overnight
  3. customThe ethyl acetate layer is separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:acetone=10:1)

Sources & evidence

ORD record
ord-5b7a0ba175774f03850e08ea6d2b92df
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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