Succinic Acid → HCID 23139072, compound

HRID 1171653Notes

Reaction equation

HRID 1171653 reaction equation
[ClH:1].[CH:2]1([C:5](=[O:27])[CH:6]([N:14]2[CH2:19][CH2:18][CH:17]([SH:20])/[C:16](=[CH:21]/[C:22]3[N:23]=[N:24][S:25][CH:26]=3)/[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])[CH2:4][CH2:3]1.[C:28](O)(=[O:34])[CH2:29][CH2:30][C:31]([OH:33])=[O:32].[I-].[K+]>CC(C)=O.Cl.O1CCOCC1>[ClH:1].[C:31]([CH2:30][CH2:29][C:28]([S:20][CH:17]1[CH2:18][CH2:19][N:14]([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])[C:5]([CH:2]2[CH2:4][CH2:3]2)=[O:27])[CH2:15]/[C:16]/1=[CH:21]\[C:22]1[N:23]=[N:24][S:25][CH:26]=1)=[O:34])([OH:33])=[O:32]

Participants

7

Reactant 3

HCID 1110Succinic Acid2×HCID 4875Potassium Iodide2×HCID 23138728HCID 23138728, compound

Product 1

HCID 23139072HCID 23139072, compoundYield 34.5%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (E)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanyl-3-[(1,2,3-thiadiazol-4-yl)methylidene]piperidine hydrochloride (100 mg) in acetone (10 ml) were added anhydrous succinic acid (26 mg) and potassium iodide (45 mg) with stirring at room temperature, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, anhydrous succinic acid (130 mg) and potassium iodide (180 mg) were further added, and the resulting mixture was furthermore stirred at room temperature for 1.5 hours. After the reaction mixture was evaporated in vacuo, the residue was purified by chromatography on a silica gel column using methanol and dichloromethane (1:50) as the eluent. The amorphous solid obtained was dissolved in a 4N solution of hydrogen chloride in dioxane (2 ml), and the resulting mixture was evaporated in vacuo to afford the title compound (40 mg, yield: 29%) as a colourless amorphous solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. stirringAfter stirring
  3. stirringthe resulting mixture was furthermore stirred at room temperature for 1.5 hours
  4. customAfter the reaction mixture was evaporated in vacuo
  5. customthe residue was purified by chromatography on a silica gel column
  6. customThe amorphous solid obtained
  7. customthe resulting mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-0f6b39b7e344406a90b4fd4b412fb109
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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