4'-Mercaptoacetanilide → HCID 178474278, compound

HRID 1987635Notes

Reaction equation

HRID 1987635 reaction equation
C1(C2CC(=O)NN=2)CCCCC1.ClC1C2C(=CC=CC=2)[N+]([O-])=CC=1.Cl[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29]/[C:28](=[C:36]2/[C:37]([CH:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[N:38][NH:39][C:40]/2=[O:41])/[CH:27]=1.[C:48]([NH:51][C:52]1[CH:57]=[CH:56][C:55]([SH:58])=[CH:54][CH:53]=1)(=[O:50])[CH3:49]>C(OC(=O)C)(=O)C.C(O)C>[CH:42]1([C:37]2=[N:38][NH:39][C:40](=[O:41])/[C:36]/2=[C:28]2\[NH:29][C:30]3[C:35]([C:26]([S:58][C:55]4[CH:54]=[CH:53][C:52]([NH:51][C:48](=[O:50])[CH3:49])=[CH:57][CH:56]=4)=[CH:27]\2)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

7

Reactant 4

HCID 707774'-MercaptoacetanilideHCID 3741098Quinoline, 4-chloro-, 1-oxideHCID 105831873-cyclohexyl-1H-pyrazol-5(4H)-oneHCID 178518891HCID 178518891, compound

Product 1

HCID 178474278HCID 178474278, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
180 °C

Procedure

3-Cyclohexyl-3-oxo-propionic acid ethyl ester (0.5 g, 2.52 mmol) was stirred in ethanol and acetic acid (10:1, 2:0.2 mL), and treated with hydrazine (0.095 mL, 3.03 mmol). After 18 hrs, the resulting solid was filtered off and washed with a minimum amount of ethanol to yield 3-cyclohexyl-1H-pyrazol-5(4H)-one. Then, the 3-cyclohexyl-1H-pyrazol-5(4H)-one (0.2 g, 1.23 mmol) and 4-chloroquinoline N-oxide (1.23 mmol) were stirred in acetic anhydride (20 mL) at ambient temperature for 60-90 minutes. The reaction mixture was concentrated and the resulting solid filtered off and washed with a minimum amount of ether. (Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-cyclohexyl-1H-pyrazol-5(4H)-one (0.05 g, 0.13 mmol) was dissolved in ethanol (1.5 mL) and 4-acetamidothiophenol (0.023 g, 0.13 mmol) was added. The reaction mixture was heated to 180° C. using a microwave reactor for 5-10 minutes. The solid was filtered and washed with ethanol to yield Example 48. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.88-1.00 (m, 2H) 1.26-1.38 (m, 2H) 1.58 (d, J=10.61 Hz, 6H) 2.10 (s, 3H) 2.33 (t, J=9.47 Hz, 1H) 6.87 (s, 1H) 7.62-7.72 (m, 3H) 7.89 (t, J=7.83 Hz, 4H) 8.17 (d, J=8.34 Hz, 1H) 10.37 (s, 1H); ESI-MS: m/z calc'd for C26H26N4O2S 458.58. found 459.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationthe resulting solid filtered off
  3. washwashed with a minimum amount of ether
  4. customfor 5-10 minutes
  5. filtrationThe solid was filtered
  6. washwashed with ethanol
  7. customto yield Example 48

Sources & evidence

ORD record
ord-0f96564eee1a4d57b1cd65bd877d2db7
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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