N-[2-(5-chloro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]acetamide → N-[2-(5-chloro-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl)ethyl]acetamide

HRID 887824Notes

Reaction equation

HRID 887824 reaction equation
[Cl:1][C:2]1[C:3]2[CH2:14][CH2:13][C:12](=[CH:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[C:4]=2[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2>O1CCCC1.[Pt]>[Cl:1][C:2]1[C:3]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[C:4]=2[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2

Participants

4

Reactant 1

HCID 68701826N-[2-(5-chloro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]acetamide

Product 1

HCID 25024914N-[2-(5-chloro-2-methyl-2,6,7,8-tetrahydrocyclopenta[e]indazol-8-yl)ethyl]acetamideYield 29.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2-(5-chloro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]acetamide (79.5 mg, 0.274 mmol) in tetrahydrofuran (5 mL) was added 5% platinum-activated carbon (32 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 7 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→25/75), liquid chromatography (water/acetonitrile=90/10→0/100) and recrystallization (ethyl acetate/hexane) to give the title compound (23.3 mg, yield 29%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→25/75), liquid chromatography (water/acetonitrile=90/10→0/100) and recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3f2b2cecf20f4d78b6b870383b0f1984
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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