4-Aminothiophenol → HCID 178440359, compound

HRID 1987613Notes

Reaction equation

HRID 1987613 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]/[C:4](=[C:12]2/[C:13]([CH2:18][CH2:19][CH3:20])=[N:14][NH:15][C:16]/2=[O:17])/[CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1>C(O)C>[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5]/[C:4](=[C:12]3/[C:13]([CH2:18][CH2:19][CH3:20])=[N:14][NH:15][C:16]/3=[O:17])/[CH:3]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 145104-AminothiophenolHCID 178440352HCID 178440352, compound

Product 1

HCID 178440359HCID 178440359, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

(Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-propyl-1H-pyrazol-5(4H)-one (0.045 g, 0.013 mmol) was dissolved in ethanol (1.5 mL) and 4-aminothiophenol (0.017 g, 0.013 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 25. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.78 (t, J=7.45 Hz, 3H) 1.30-1.40 (m, 2H) 2.22-2.32 (m, 2H) 6.77 (d, J=8.34 Hz, 3H) 7.33 (d, J=8.59 Hz, 2H) 7.60 (t, J=7.33 Hz, 1H) 7.82-7.92 (m, 2H) 8.12 (d, J=8.08 Hz, 1H); ESI-MS: m/z calc'd for C21H20N4OS 376.47. found 377.2 (M+H)+.

Workup

  1. customfor 5-10 minutes
  2. concentrationThe mixture was then concentrated
  3. custompurified by LC-MS
  4. customto give Example 25

Sources & evidence

ORD record
ord-db6636447be44e5b8f4f68abd0d0caf6
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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