HCID 69309210, compound → HCID 69311654, compound

HRID 860476Notes

Reaction equation

HRID 860476 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[C:16]3[N:17]([C:31]([CH2:34][CH3:35])=[CH:32][CH:33]=3)[N:18]=[C:19]([CH3:30])[C:20]=2[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:12]=[N:13][CH:14]=1)=O)(C)(C)C>C(OC(=O)C)C.Cl>[NH2:8][C:9]1[CH:10]=[C:11]([C:15]2[C:16]3[N:17]([C:31]([CH2:34][CH3:35])=[CH:32][CH:33]=3)[N:18]=[C:19]([CH3:30])[C:20]=2[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:12]=[N:13][CH:14]=1

Participants

3

Reactant 1

HCID 69309210HCID 69309210, compound

Product 1

HCID 69311654HCID 69311654, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

A solution of ethyl 5-(4-{5-[(tert-butoxycarbonyl)amino]-3-pyridinyl}-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl)pentanoate (190 mg) in 2 N hydrogen chloride ethyl acetate solution (4 mL) was stirred at ambient temperature for 2 hours. After evaporation of solvent, the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. 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 chloroform and methanol (100:1–20:1) to give ethyl 5-[4-(5-amino-3-pyridinyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate as yellow oil (140 mg)

Workup

  1. customAfter evaporation of solvent
  2. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a mixture of chloroform and methanol (100:1–20:1)

Sources & evidence

ORD record
ord-378ece63e8c543d48fa2bd105f1d694d
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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