HCID 86643706, compound → HCID 67352368, compound

HRID 1672844Notes

Reaction equation

HRID 1672844 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N+:11]([O-])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:29][C@H:28]4[N:24]([CH2:25][CH2:26][CH2:27]4)[C:23]4[N:30]=[C:31]([NH:34][CH2:35][CH3:36])[N:32]=[CH:33][C:22]=4[C:21]3=[O:37])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([N:20]3[CH2:29][C@H:28]4[N:24]([CH2:25][CH2:26][CH2:27]4)[C:23]4[N:30]=[C:31]([NH:34][CH2:35][CH3:36])[N:32]=[CH:33][C:22]=4[C:21]3=[O:37])[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 86643706HCID 86643706, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67352368HCID 67352368, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(S)-4-Tert-butoxycarbonyl-1-[3-(9-ethylamino-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]piperazine-1-oxide (0.338 g, 0.645 mmol) obtained in Step 2 was dissolved in ethanol (10 mL), and the mixture was stirred for 1.5 hours under a stream of hydrogen gas after adding 10% palladium-on-carbon (137 mg, 0.0646 mmol). The mixture was filtered through sellite, and the filtrate was concentrated to give (S)-5-[3-(4-tert-butoxycarbonylpiperazine-1-yl)phenyl]-9-ethylamino-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (0.235 g, 72%).

Workup

  1. filtrationThe mixture was filtered through sellite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-41f1401687964a21ab81db1bb87b6f82
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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