HCID 59513633, compound → HCID 24900807, compound

HRID 1158746Notes

Reaction equation

HRID 1158746 reaction equation
C(OC(=O)[NH:10][C@H:11]([CH3:30])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]2[CH:22]=[C:23]([C:27]([NH2:29])=[O:28])[C:24]([NH2:26])=[N:25][C:14]1=2)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:26][C:24]1[C:23]([C:27]([NH2:29])=[O:28])=[CH:22][C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]([CH2:12][C@H:11]([NH2:10])[CH3:30])[C:14]=2[N:25]=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): Δ 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-9b31031ff7bf40df8bbdb73a851875b1
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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