4-(4-Acetylaminophenyl)-1,2-Dihydro-1-Methyl-2-Ethylcarbamoyl-6-Methylthiophthalazine → HCID 9841541, compound

HRID 48179Notes

Reaction equation

HRID 48179 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([S:21][CH3:22])[CH:19]=3)[CH:14]([CH3:23])[N:13]([C:24](=[O:28])[NH:25][CH2:26][CH3:27])[N:12]=2)=[CH:7][CH:6]=1)(=O)C>CO.[OH-].[Na+].O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([S:21][CH3:22])[CH:19]=3)[CH:14]([CH3:23])[N:13]([C:24](=[O:28])[NH:25][CH2:26][CH3:27])[N:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 1

HCID 129861734-(4-Acetylaminophenyl)-1,2-Dihydro-1-Methyl-2-Ethylcarbamoyl-6-Methylthiophthalazine

Product 1

HCID 9841541HCID 9841541, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

The solution of acetyl amide 9 in methanol and NaOH (2 N) was refluxing until there is no more starting material left monitored by TLC. The solution was diluted with water, and extracted with DCM three times. Removal of the solvent afforded the crude product, which was purified by using a silica gel column, gave the desired products 12 (Yield: 87%). 1HNMR (CDCl3): 7.45 (d, J=8.6 Hz, 2H), 7.35-7.25 (m, 4H), 6.78 (d, J=8.6 Hz, 2H), 6.53 (br, 1H), 5.60 (q, J=13.2 Hz, 1H), 3.42 (m, 2H), 2.40 (s, 3H), 1.22 (m, 6H).

Workup

  1. waitleft
  2. extractionextracted with DCM three times
  3. customRemoval of the solvent
  4. customafforded the crude product, which
  5. customwas purified

Sources & evidence

ORD record
ord-dac157113b8b4855a374a0ee0f45e116
Source dataset
uspto-grants-2004_03
Patent number
US06703390B2

Reaction notes

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