HCID 118036935, compound → HCID 118037283, compound

HRID 1508974Notes

Reaction equation

HRID 1508974 reaction equation
[ClH:1].[C:2]1([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][C:10]3=[C:9]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]([NH2:26])=[O:25])=[CH:19][CH:18]=3)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH:3]=1>C(O)C.[Pd]>[ClH:1].[CH:2]1([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][C:10]3=[C:9]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]([NH2:26])=[O:25])=[CH:19][CH:18]=3)[CH:8]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 118036935HCID 118036935, compound

Product 1

HCID 118037283HCID 118037283, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(4-((2-(cyclopent-1-en-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetamide hydrochloride (0.042 g, 0.11 mmol) in ethanol (10 mL) was added 10% palladium on carbon (0.005 g). The mixture stirred at rt for 2 h under an atmosphere of hydrogen. After this time, the mixture was filtered over celite, concentrated, and the residue converted to the hydrochloride salt to afford the title compound (0.040 g, 95%) as a white solid. MW=420.38. 1H NMR (DMSO-d6, 500 MHz) δ 13.60 (s, 1H), 9.59 (s, 1H), 7.52 (s, 1H), 7.36 (d, J=8.0 Hz, 1H), 7.26 (d, J=8.0 Hz, 2H), 6.92 (s, 1H), 6.69-6.66 (m, 1H), 3.42 (s, 1H), 3.18-3.04 (m, 3H), 2.83 (t, J=7.5 Hz, 2H), 2.18 (quin, J=7.5 Hz, 2H), 2.07-1.96 (m, 2H), 1.77-1.69 (m, 2H), 1.68-1.52 (m, 4H), 1.37-1.22 (m, 2H); APCI MS m/z 384 [M+H]+.

Workup

  1. filtrationAfter this time, the mixture was filtered over celite,
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a419d11dcdac4e2b8a0ddf61b69c8265
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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