Tetrahydrofuran → HCID 69311621, compound

HRID 2250590Notes

Reaction equation

HRID 2250590 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 2.5 hours at room temperature. The mixture was stirred for further 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 further 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-9ccaa8aba8214eb7acb2188e5259b5c7
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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