Hydrochloric Acid → HCID 59762220, compound

HRID 1771902Notes

Reaction equation

HRID 1771902 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-cea4dbd45d364d2fac0bcaf5e6e8277e
Source dataset
uspto-grants-2016_02
Patent number
US09249147B2

Reaction notes

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