Hydrochloric Acid → HCID 69307054, compound

HRID 860432Notes

Reaction equation

HRID 860432 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[N:10]([C:29]([CH2:32][CH3:33])=[CH:30][CH:31]=3)[N:11]=[C:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]=2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])[CH:5]=[CH:4][N:3]=1.[CH3:34][S-:35].[Na+].Cl>C1(C)C=CC=CC=1.O1CCCC1>[CH2:32]([C:29]1[N:10]2[N:11]=[C:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([S:35][CH3:34])[CH:7]=3)[C:9]2=[CH:31][CH:30]=1)[CH3:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 86597468HCID 86597468, compound

Product 1

HCID 69307054HCID 69307054, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-[4-(2-chloro-4-pyridinyl)-7-ethyl-2-phenylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate (120 mg) in toluene (5 mL) and tetrahydrofuran (10 mL) was added sodium thiomethoxide (91.0 mg) and the mixture was heated under reflux for 4 hours. The solution was acidfied with 1N hydrochloric acid and extracted with chloroform. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (10:1–3:1) to give 5-{7-ethyl-4-[2-(methylthio)-4-pyridinyl]-2-phenylpyrrolo-[1,2-b]pyridazin-3-yl}pentanoic acid as an yellow powder (85.0 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionextracted with chloroform
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a mixture of hexane and ethyl acetate (10:1–3:1)

Sources & evidence

ORD record
ord-7c8fba54eff54b3c947c643cf7651048
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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