4'-Mercaptoacetanilide → HCID 178487269, compound

HRID 1987633Notes

Reaction equation

HRID 1987633 reaction equation
C1(C2CC(=O)NN=2)CC1.ClC1C2C(=CC=C(OC)C=2)[N+]([O-])=CC=1.Cl[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=2)[NH:28]/[C:27](=[C:37]2/[C:38]([CH:43]3[CH2:45][CH2:44]3)=[N:39][NH:40][C:41]/2=[O:42])/[CH:26]=1.[C:46]([NH:49][C:50]1[CH:55]=[CH:54][C:53]([SH:56])=[CH:52][CH:51]=1)(=[O:48])[CH3:47]>C(OC(=O)C)(=O)C.C(O)C>[CH:43]1([C:38]2=[N:39][NH:40][C:41](=[O:42])/[C:37]/2=[C:27]2\[NH:28][C:29]3[C:34]([C:25]([S:56][C:53]4[CH:52]=[CH:51][C:50]([NH:49][C:46](=[O:48])[CH3:47])=[CH:55][CH:54]=4)=[CH:26]\2)=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[CH2:45][CH2:44]1

Participants

7

Reactant 4

HCID 707774'-MercaptoacetanilideHCID 220594943-cyclopropyl-4,5-dihydro-1H-pyrazol-5-oneHCID 690548584-Chloro-6-methoxyquinoline 1-oxideHCID 178487191HCID 178487191, compound

Product 1

HCID 178487269HCID 178487269, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
180 °C

Procedure

3-Cyclopropyl-1H-pyrazol-5(4H)-one (0.2 mmol) and 4-chloro-6-methoxyquinoline 1-oxide (0.025 g, 0.2 mmol) were stirred in acetic anhydride (1.5 mL) at ambient temperature for 30-40 minutes. The reaction mixture was concentrated and the resulting solid filtered off and washed with a minimum amount of ether. (Z)-4-(4-chloro-6-methoxyquinolin-2(1H)-ylidene)-3-cyclopropyl-1H-pyrazol-5(4H)-one (0.04 g, 0.11 mmol) was dissolved in ethanol (1.5 mL) and 4-acetamidothiophenol (0.019 g, 0.11 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 the resulting solid filtered and washed with ether to give Example 47. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.46 (d, J=6.57 Hz, 2H) 0.65-0.71 (m, 2H) 1.43-1.54 (m, 1H) 2.11 (s, 3H) 3.98 (s, 3H) 7.18 (s, 1H) 7.45 (d, J=2.53 Hz, 1H) 7.63 (dd, J=9.09, 2.27 Hz, 1H) 7.70 (d, J=8.59 Hz, 2H) 7.82 (d, J=8.59 Hz, 2H) 8.07 (d, J=9.09 Hz, 1H) 10.39 (s, 1H); ESI-MS: m/z calc'd for C24H22N4O3S 446.52. found 447.2 (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. concentrationThe mixture was then concentrated
  6. filtrationthe resulting solid filtered
  7. washwashed with ether
  8. customto give Example 47

Sources & evidence

ORD record
ord-5bd207f2dbeb480eb4112ce36be9964a
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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