HCID 59513633, compound → HCID 24900807, compound

HRID 421655Notes

Reaction equation

HRID 421655 reaction equation
[NH2:1][C:2]1[C:3]([C:29]([NH2:31])=[O:30])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C@H:15]([NH:17]C(=O)OCC3C=CC=CC=3)[CH3:16])[C:6]=2[N:28]=1>C(O)C.[Pd]>[NH2:1][C:2]1[C:3]([C:29]([NH2:31])=[O:30])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C@H:15]([NH2:17])[CH3:16])[C:6]=2[N:28]=1

Participants

4

Reactant 1

HCID 59513633HCID 59513633, compound

Product 1

HCID 24900807HCID 24900807, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl {(1R)-2-[2-amino-3-(aminocarbonyl)-9H-pyrido[2,3-b]indol-9-yl]-1-methylethyl}carbamate (xxiv-a, 13 mg, 0.031 mmol) in ethanol (10 mL) was added palladium on carbon (10 mg, 0.094 mmol). The reaction mixture was stirred under a hydrogen atmosphere overnight. Solids were removed by filtration and the filtrate was concentrated in vacuo to afford 2-amino-9-[(2R)-2-aminopropyl]-9H-pyrido[2,3-b]indole-3-carboxamide (35, 7.6 mg, 86%). NH4OAc standard conditions. DAD Retention time=4.90 min. M+H=284. 1H NMR (300 MHz, MeOD-d4): 8.66 (s, 1H), 7.90 (d, J=7.7 Hz, 1H) 7.49 (d, J=8.1 Hz, 1H), 7.23 (ddd, J=7.4, 6.9, 1.2 Hz, 1H), 7.17 (ddd, J1=7.8, 7.7, 1.2 Hz, 1H), 4.33 (d, J=6.1 Hz, 2H), 3.63-3.71 (m, 1H), 1.23 (d, J=6.5 Hz, 3H).

Workup

  1. customSolids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ade8034f404745289064eb8d7e513bed
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

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