Hydrochloric Acid → HCID 178433890, compound

HRID 418003Notes

Reaction equation

HRID 418003 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14](=[C:17]([NH:19][NH:20][C:21]([N:23]3[CH2:28][CH2:27][CH:26]([C:29]([O:31]C)=[O:30])[CH2:25][CH2:24]3)=[S:22])[CH3:18])[C:13]([CH3:33])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.O>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15](=[O:16])[C:14](=[C:17]([NH:19][NH:20][C:21]([N:23]3[CH2:24][CH2:25][CH:26]([C:29]([OH:31])=[O:30])[CH2:27][CH2:28]3)=[S:22])[CH3:18])[C:13]([CH3:33])=[N:12]2)=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 178498452HCID 178498452, compound

Product 1

HCID 178433890HCID 178433890, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-(N′-{1-[1-(4-t-butylphenyl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-ethyl}-hydrazinothiocarbonyl)-piperidine-4-carboxylate (89.6 mg, 0.190 mmol) in methanol (3.0 mL) was stirred with 1 M aqueous sodium hydroxide (570 μL, 0.570 mmol) at room temperature for 11 hours, with 1 M aqueous sodium hydroxide (380 μL, 0.380 mmol) at room temperature for 3 hours and then with 1 M hydrochloric acid (950 μL, 0.950 mmol) and water at room temperature for another 30 minutes. The resulting precipitate was collected by filtration, washed with water and methanol and dried under reduced pressure to give 47.7 mg of the desired product (55% yield).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water and methanol
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-5fb1cc21a2a04b47ade3be1b3c5a8042
Source dataset
uspto-grants-2012_01
Patent number
US08093251B2

Reaction notes

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