HCID 69306898, compound → HCID 69306999, compound

HRID 2250591Notes

Reaction equation

HRID 2250591 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-7e20ed0ce3f44158b99b2bf717c61aac
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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