HCID 69311557, compound → HCID 69311686, compound

HRID 860515Notes

Reaction equation

HRID 860515 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]2[C:16]3[N:17]([C:28]([CH2:31][CH3:32])=[CH:29][CH:30]=3)[N:18]=[C:19]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:20]=2[C:21]#[N:22])[CH:14]=1)[C:5]([O:7]C(C)(C)C)=[O:6]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]2[C:16]3[N:17]([C:28]([CH2:31][CH3:32])=[CH:29][CH:30]=3)[N:18]=[C:19]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:20]=2[C:21]#[N:22])[CH:14]=1)[C:5]([OH:7])=[O:6]

Participants

3

Reactant 1

HCID 69311557HCID 69311557, compound

Product 1

HCID 69311686HCID 69311686, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 3-bromo-5-[3-cyano-7-ethyl-2-(1-pyrrolidinyl)pyrrolo[1,2-b]pyridazin-4-yl]benzoate (16.0 mg) in trifluoroacetic acid (0.5 mL) was stirred for 0.5 hour at room temperature. The reaction was quenched by adding water. The mixture was neutralized by adding NaOH (pH=3). The mixture was extracted with EtOAc. The extract was washed with brine, dried over MgSO4, and evaporated to give a greenish yellow solid. The solid was triturated in hexanes-CHCl3 (2-1) to afford 3-bromo-5-[3-cyano-7-ethyl-2-(1-pyrrolidinyl)pyrrolo[1,2-b]pyridazin-4-yl]benzoic acid as an yellow powder (10.8 mg).

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. additionby adding NaOH (pH=3)
  4. extractionThe mixture was extracted with EtOAc
  5. washThe extract was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give a greenish yellow solid
  9. customThe solid was triturated in hexanes-CHCl3 (2-1)

Sources & evidence

ORD record
ord-480c1b1cc4594c95b53e9eb85c39a79d
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

Loading…