4'-Mercaptoacetanilide → HCID 178440345, compound

HRID 1987642Notes

Reaction equation

HRID 1987642 reaction equation
CN1C(=O)CC(CCC)=N1.ClC1C2C(=CC=CC=2)[N+]([O-])=CC=1.Cl[C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27]/[C:26](=[C:34]2/[C:35]([CH2:41][CH2:42][CH3:43])=[N:36][N:37]([CH3:40])[C:38]/2=[O:39])/[CH:25]=1.[C:44]([NH:47][C:48]1[CH:53]=[CH:52][C:51]([SH:54])=[CH:50][CH:49]=1)(=[O:46])[CH3:45]>C(OC(=O)C)(=O)C.C(O)C>[CH3:40][N:37]1[C:38](=[O:39])/[C:34](=[C:26]2\[NH:27][C:28]3[C:33]([C:24]([S:54][C:51]4[CH:50]=[CH:49][C:48]([NH:47][C:44](=[O:46])[CH3:45])=[CH:53][CH:52]=4)=[CH:25]\2)=[CH:32][CH:31]=[CH:30][CH:29]=3)/[C:35]([CH2:41][CH2:42][CH3:43])=[N:36]1

Participants

7

Reactant 4

HCID 707774'-MercaptoacetanilideHCID 5205161-Methyl-3-n-propyl-2-pyrazolin-5-oneHCID 3741098Quinoline, 4-chloro-, 1-oxideHCID 178440343HCID 178440343, compound

Product 1

HCID 178440345HCID 178440345, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
180 °C

Procedure

1-Methyl-3-n-propyl 2-pyrazolin-5-one (0.2 g, 1.4 mmol) and 4-chloroquinoline N-oxide (1.4 mmol) were stirred in acetic anhydride (2 mL) at ambient temperature for 2-3 hours. The reaction mixture was concentrated and carried out to the next step without further purification. The resulting (Z)-4-(4-chloroquinolin-2(1H)-ylidene)-1-methyl-3-propyl-1H-pyrazol-5(4H)-one (0.71 mmol) was dissolved in ethanol (0.5 mL) and 4-acetamidothiophenol (0.13 g, 0.78 mmol) was added. The reaction mixture was heated to 180° C. using a microwave reactor for 5-10 minutes. The mixture was then concentrated and purified by LC-MS to give Example 56. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.67 (t, J=7.45 Hz, 3H) 1.23-1.32 (m, J=7.52, 7.52, 7.52, 7.52 Hz, 2H) 2.00 (t, J=7.58 Hz, 2H) 2.09 (s, 3H) 3.29 (s, 3H) 6.53 (s, 1H) 7.52-7.57 (m, 1H) 7.67-7.76 (m, 3H) 7.80-7.90 (m, 3H) 8.06 (d, J=8.08 Hz, 1H) 10.34 (s, 1H); ESI-MS: m/z calc'd for C24H24N4O2S 432.54. found 433.3 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customcarried out to the next step without further purification
  3. customfor 5-10 minutes
  4. concentrationThe mixture was then concentrated
  5. custompurified by LC-MS
  6. customto give Example 56

Sources & evidence

ORD record
ord-c270657855e645679d3d3de02ab1132b
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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