Tetrahydrofuran → HCID 69311621, compound

HRID 860448Notes

Reaction equation

HRID 860448 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[N:11]([C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=3)[N:12]=[C:13]([CH2:20][C:21]([O:23]CC)=[O:22])[C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1)#[N:2].O1CCCC1.[OH-].[K+]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10]3[N:11]([C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=3)[N:12]=[C:13]([CH2:20][C:21]([OH:23])=[O:22])[C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium Hydroxide2×HCID 69308255HCID 69308255, compound

Product 1

HCID 69311621HCID 69311621, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(4-cyanophenyl)-2-(2-ethoxy-2-oxoethyl)-7-ethylpyrrolo[1,2-b]pyridazine-3-carboxylate (77.9 mg) in ethanol (0.5 mL)-tetrahydrofuran (0.5 mL) was added 1N potassium hydroxide. The resulting solution was stirred for 25 hours at room temperature. The mixture was stirred for futher 1 hour after adding 1N potassium hydroxide (0.04 mL). The reaction was quenched by adding 1N hydrochloric acid (0.23 mL). The volatile was evaporated off, and the resulting residue was partitioned between ethyl acetate (10 mL) and 1N hydrochloric acid (6 mL). The organic layer was washed with brine, dried, and evaporated to give [4-(4-cyanophenyl)-3-(ethoxycarbonyl)-7-ethylpyrrolo[1,2-b]pyridazin-2-yl]acetic acid as an yellow solid (67.7 mg, 93.4%).

Workup

  1. stirringThe mixture was stirred for futher 1 hour
  2. customThe reaction was quenched
  3. additionby adding 1N hydrochloric acid (0.23 mL)
  4. customThe volatile was evaporated off
  5. customthe resulting residue was partitioned between ethyl acetate (10 mL) and 1N hydrochloric acid (6 mL)
  6. washThe organic layer was washed with brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-dbfc69dbf22f405abbad21d2a83201ff
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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