Hydrochloric Acid → HCID 42606028, compound

HRID 448509Notes

Reaction equation

HRID 448509 reaction equation
[N:1]([CH2:4][C:5]([NH:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10](=[O:27])[N:11]([C:18]1([CH3:26])[CH2:23][CH2:22][C:21](=[O:24])[NH:20][C:19]1=[O:25])[C:12]2=[O:17])=[O:6])=[N+]=[N-].O.[ClH:29]>CO.[Pd]>[ClH:29].[NH2:1][CH2:4][C:5]([NH:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10](=[O:27])[N:11]([C:18]1([CH3:26])[CH2:23][CH2:22][C:21](=[O:24])[NH:20][C:19]1=[O:25])[C:12]2=[O:17])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86607662HCID 86607662, compound

Product 1

HCID 42606028HCID 42606028, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-azido-N-[2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-acetamide (1.4 g, 3.8 mmol) and 10% Pd/C (0.2 g) in methanol (100 mL) and 4N HCl (20 mL) was hydrogenated in Parr Shaker for 5 hours. H2O (10 mL) was added, and the mixture was filtered through celite. The filtrate was concentrated, and the residue was evaporated with ethanol (3×20 mL). The solid was slurried with hot methanol (30 mL) to give 2-amino-N-[2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-acetamide hydrochloride (0.5 g, 35%) as a yellow solid: mp 111-113° C.; 1H NMR (DMSO-d6) δ 1.90 (s, 3H, CH3), 2.04-2.09 (m, 1H), 2.50-2.72 (m, 3H), 3.97 (s, 2H, CH2), 7.64 (d, J=7.2 Hz, 1H, Ar), 7.86 (t, J=7.7 Hz, 1H, Ar), 8.32 (d, J=8.2 Hz, 1H, Ar), 8.40 (s, 3H, NH3), 10.30 (s, 1H, NH), 11.05 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.05, 28.55, 29.10, 41.11, 58.83, 117.98, 118.92, 127.13, 131.76, 134.74, 135.99, 166.18, 167.22, 167.75, 172.04, 172.18; Anal. calcd. for C16H17N4O5Cl: C, 50.47; H, 4.50; N, 14.71; Cl, 9.31. Found: C, 50.35; H, 4.40; N, 14.54; Cl, 9.01.

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was evaporated with ethanol (3×20 mL)

Sources & evidence

ORD record
ord-0647fb71d55b4ee59b13c8e6fe2c17e9
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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