HCID 69306898, compound → HCID 69306999, compound

HRID 860449Notes

Reaction equation

HRID 860449 reaction equation
[CH2:1]([C:3]1[N:7]2[N:8]=[C:9]3[C:22](=[O:23])[CH2:21][S:20](=[O:25])(=[O:24])[C:10]3=[C:11]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[C:6]2=[CH:5][CH:4]=1)[CH3:2]>O1CCCC1>[CH2:1]([C:3]1[N:7]2[N:8]=[C:9]3[CH:22]([OH:23])[CH2:21][S:20](=[O:24])(=[O:25])[C:10]3=[C:11]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[C:6]2=[CH:5][CH:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 69306898HCID 69306898, compound

Product 1

HCID 69306999HCID 69306999, compoundYield 954.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(6-ethyl-1,1-dioxido-3-oxo-2,3-dihydropyrrolo[1,2-b]thieno[2,3-e]pyridazin-9-yl)benzonitrile (60.0 mg) in tetrahydrofuran (0.2 mL) was added 1 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (0.487 mL) under an ice-bath. After stirring for 1 hour, the reaction was quenched by adding 1N hydrochloric acid (1 mL). The mixture was partitioned between ethyl acetate (20 mL) and water (10 mL), and the organic layer was washed with brine, dried, and evaporated to give 3-(6-ethyl-3-hydroxy-1,1-dioxido-2,3-dihydropyrrolo[1,2-b]thieno[2,3-e]pyridazin-9-yl)-benzonitrile as an yellow foam (576 mg, 99.8%).

Workup

  1. customthe reaction was quenched
  2. additionby adding 1N hydrochloric acid (1 mL)
  3. customThe mixture was partitioned between ethyl acetate (20 mL) and water (10 mL)
  4. washthe organic layer was washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-beb5a23f4a0d4c0794dbd90b770384c6
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

Loading…