Hydrazine → HCID 178507798, compound

HRID 1987603Notes

Reaction equation

HRID 1987603 reaction equation
C1(C(=O)CC(O)=O)CC1.NN.[CH:12]1([C:15]2[CH2:19][C:18](=[O:20])[NH:17][N:16]=2)[CH2:14][CH2:13]1.Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N+:25]([O-])=[CH:24][CH:23]=1.C([NH:36][C:37]1[CH:42]=[CH:41][C:40]([SH:43])=[CH:39][CH:38]=1)(=O)C>C(O)C.C(OC(=O)C)(=O)C.C(O)(=O)C>[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([S:43][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25]/[C:24](=[C:19]3/[C:15]([CH:12]4[CH2:14][CH2:13]4)=[N:16][NH:17][C:18]/3=[O:20])/[CH:23]=2)=[CH:39][CH:38]=1

Participants

9

Reactant 5

HCID 9321HydrazineHCID 707774'-MercaptoacetanilideHCID 3741098Quinoline, 4-chloro-, 1-oxideHCID 219358503-Cyclopropyl-3-oxopropanoic acidHCID 220594943-cyclopropyl-4,5-dihydro-1H-pyrazol-5-one

Product 1

HCID 178507798HCID 178507798, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
180 °C

Procedure

3-Cyclopropyl-3-oxo-propionic acid (0.5 g, 3.2 mmol) was stirred in ethanol and acetic acid (10:1, 2.2 mL) and treated with hydrazine (0.12 mL, 3.8 mmol). After 15 hrs, the solid was filtered off and washed with a minimum amount of ethanol. Then, the product (3-cyclopropyl-1H-pyrazol-5(4H)-one) (0.4 mmol) and 4-chloroquinoline N-oxide (0.087 g, 0.48 mmol) were stirred in acetic anhydride (1 mL) at ambient temperature for 20-30 minutes. The reaction mixture was concentrated and carried out to the next step with out any purification. The resulting (Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-cyclopropyl-1H-pyrazol-5(4H)-one was dissolved in ethanol (1.5 mL) and 4-acetamidothiophenol (0.076 g, 0.45 mmol) was added. The reaction mixture was heated to 180° C. using a microwave reactor for 30 minutes. The mixture was concentrated and purified by LC-MS to give the title compounds of Example 14 and Example 15.

Workup

  1. filtrationthe solid was filtered off
  2. washwashed with a minimum amount of ethanol
  3. concentrationThe reaction mixture was concentrated
  4. customcarried out to the next step with out any purification
  5. dissolutionThe resulting (Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-cyclopropyl-1H-pyrazol-5(4H)-one was dissolved in ethanol (1.5 mL)
  6. customfor 30 minutes
  7. concentrationThe mixture was concentrated
  8. custompurified by LC-MS

Sources & evidence

ORD record
ord-a01da17d4607431c9a0f1feef7d5716c
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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