Hydrochloric Acid → HCID 59762220, compound

HRID 2409504Notes

Reaction equation

HRID 2409504 reaction equation
[NH2:1][C:2]1[C:3]([Cl:23])=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[N:6]([CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[C:5]2=[O:22].CC(O)C.Cl.CO>O1CCOCC1.[Pd]>[NH2:1][C:2]1[C:3]([Cl:23])=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[C:7](=[O:14])[N:6]([CH:15]1[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]1)[C:5]2=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3776IsopropanolHCID 59761951HCID 59761951, compound

Product 1

HCID 59762220HCID 59762220, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 5-amino-4-chloro-2-(1-methyl-piperidin-4-yl)-6-nitro-isoindole-1,3-dione (1.35 g, not pure) and 10% Pd/C (500 mg) was added 2-propanol (20 mL), HCl in dioxane (4 M, 0.1 mL) and then MeOH (230 mL). After it was stirred under atmospheric hydrogen for 1.5 h, the reaction mixture was filtered over Celite. The filtrate was concentrated, diluted with 50% DCM in MeOH, basified with aqueous NH4OH solution (28%) and evaporated. Chromatography of the mixture with mixed solvent of CH2Cl2/MeOH/28% aqueous NH4OH (50:10:1) afforded the title compound (186 mg, 6% for 2 steps). 1H NMR (DMSO-d6) δ 1.51 (m, 2H), 1.90 (m, 2H), 2.29 (m, 2H), 2.81 (m, 2H), 3.80 (m, 1H), 5.61 (br s, 2H, NH2), 5.93 (br s, 2H, NH2), 6.82 (s, 1H, ArH); ESI-MS m/z 309.4 (MH+).

Workup

  1. filtrationthe reaction mixture was filtered over Celite
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with 50% DCM in MeOH
  4. customevaporated

Sources & evidence

ORD record
ord-ceb59c862d1041acac32568c36f43a7f
Source dataset
uspto-grants-2014_08
Patent number
US08815906B2

Reaction notes

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