HCID 57509668, compound → HCID 57509898, compound

HRID 624113Notes

Reaction equation

HRID 624113 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:27])[NH:23][CH2:24][CH2:25][CH3:26])=[CH:18][CH:17]=1)=[O:14])[CH2:7]2)([O-])=O.[H][H]>CN(C)C=O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:27])[NH:23][CH2:24][CH2:25][CH3:26])=[CH:18][CH:17]=1)=[O:14])[CH2:7]2

Participants

5

Reactant 2

HCID 57509668HCID 57509668, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57509898HCID 57509898, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-nitro-N-[4-(propylcarbamoyl)phenyl]-1,3-dihydro-2H-isoindole-2-carboxamide (37 mg, 0.1 mmol) in 1 ml dimethylformamide in the presence of 11 mg of 10% Pd on carbon was treated with a hydrogen balloon overnight at room temperature. The suspension was filtered through diatomaceous earth and purified by reverse-phase HPLC to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.51 (s, 1H), 8.24 (t, J=5.6 Hz, 1H), 7.74-7.78 (m, 2H), 7.62-7.66 (m, 2H), 7.19 (d, J=7.9 Hz, 1H), 6.78-6.89 (m, 2H), 4.67-4.71 (m, 4H), 3.15-3.26 (m, 2H), 1.46-1.59 (m, 2H), 0.89 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 339 (M+H)+.

Workup

  1. filtrationThe suspension was filtered through diatomaceous earth
  2. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-86cf1e293bef4aa48437d6ed411ae500
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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