Hydrochloric Acid → 5-(6-methoxy-1-oxoisoindolin-2-yl)-N-(4-(piperazin-1-yl)pyridin-3-yl)furan-2-carboxamide

HRID 1184525Notes

Reaction equation

HRID 1184525 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][N:8]([C:13]3[O:17][C:16]([C:18]([NH:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][C:26]=4[N:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)=[O:19])=[CH:15][CH:14]=3)[C:9]2=[O:12])=[CH:5][CH:4]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][N:8]([C:13]3[O:17][C:16]([C:18]([NH:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][C:26]=4[N:27]4[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]4)=[O:19])=[CH:15][CH:14]=3)[C:9]2=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68161686Tert-butyl 4-(3-(5-(6-methoxy-1-oxoisoindolin-2-yl)furan-2-carboxamido)pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 670515055-(6-methoxy-1-oxoisoindolin-2-yl)-N-(4-(piperazin-1-yl)pyridin-3-yl)furan-2-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The Example 1 compound, tert-butyl 4-(3-(5-(6-methoxy-1-oxoisoindolin-2-yl)furan-2-carboxamido)pyridin-4-yl)piperazine-1-carboxylate (1.5) (0.1 mmol) was cooled to 0° C. in 1 mL of dioxane and was added to 4N HCl in dioxane (1 mL) and stirred at room temperature for 30 min. Dioxane was removed under vacuo, redissolved in water-acetonitrile and freezed and lyophilized to obtain 5-(6-methoxy-1-oxoisoindolin-2-yl)-N-(4-(piperazin-1-yl)pyridin-3-yl)furan-2-carboxamide (Example 1) as white powder. HPLC-MS tR=0.75 min (UV254 nm); Mass calculated for formula C23H23N5O4, 433.18, observed LCMS m/z 434.20 (M+H)

Workup

  1. customDioxane was removed under vacuo
  2. dissolutionredissolved in water-acetonitrile

Sources & evidence

ORD record
ord-9dff0b9dd6b54e6ca86e9c5fdca8173a
Source dataset
uspto-grants-2014_03
Patent number
US08669259B2

Reaction notes

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