Pyridine → HCID 57509907, compound

HRID 624118Notes

Reaction equation

HRID 624118 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:25])[NH:21][CH2:22][CH2:23][CH3:24])=[CH:16][CH:15]=1)=[O:12])[CH2:5]2.N1C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>CN(C)C=O>[CH3:32][S:33]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:25])[NH:21][CH2:22][CH2:23][CH3:24])=[CH:16][CH:15]=1)=[O:12])[CH2:5]2)(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 57509898HCID 57509898, compound

Product 1

HCID 57509907HCID 57509907, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide (0.035 g, 0.103 mmol), pyridine (0.017 mL, 0.207 mmol) and catalytic N,N-dimethylaminopyridine in dimethylformamide (0.7 mL) was cooled to 0° C. Methanesulfonyl chloride (0.014 g, 0.126 mmol) was added and the reaction solution was allowed to stir at room temperature for 2 hours. The reaction mixture was concentrated and purified by reverse-phase HPLC to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.74 (s, 1H), 8.54 (s, 1H), 8.26 (t, J=5.6 Hz, 1H), 7.74-7.78 (m, 2H), 7.63-7.66 (m, 2H), 7.32 (d, J=8.1 Hz, 1H), 7.14-7.20 (m, 2H), 4.73-4.76 (m, 4H), 3.15-3.25 (m, 2H), 2.98 (s, 3H), 1.45-1.62 (m, 2H), 0.89 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 417 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-610e94c9d2644f38a5acd7155fbb4679
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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