HCID 437068, compound → N-(4-{[(3-methoxybenzyl)sulfonyl]amino}phenyl)-1,3-dihydro-2H-isoindole-2-carboxamide

HRID 624235Notes

Reaction equation

HRID 624235 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C(C(C(C)C)(C(C)C)CN)(C)C.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH2:40][S:41](Cl)(=[O:43])=[O:42])[CH:37]=[CH:38][CH:39]=1>ClCCl>[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:37]=[CH:38][CH:39]=1)[CH2:40][S:41]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:10])=[CH:6][CH:7]=1)(=[O:42])=[O:43]

Participants

5

Reactant 3

HCID 437068HCID 437068, compoundHCID 23211153(3-Methoxyphenyl)methanesulfonyl chlorideHCID 62231518N-(4-aminophenyl)isoindoline-2-carboxamide

Product 1

HCID 57510466N-(4-{[(3-methoxybenzyl)sulfonyl]amino}phenyl)-1,3-dihydro-2H-isoindole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(4-aminophenyl)isoindoline-2-carboxamide (0.0585 g, 0.231 mmol) was suspended in dichloromethane (2 ml) followed by addition of triisopropylethylamine (0.081 ml, 0.462 mmol). (3-Methoxyphenyl)methanesulfonyl chloride (0.061 g, 0.277 mmol) was dissolved in 1 ml dichloromethane and added to the mixture via syringe slowly. The mixture was quenched with water and the separated aqueous layer was extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated. Reverse-phase HPLC provided the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.65 (s, 1H), 8.61 (s, 1H), 8.50 (d, J=5.0 Hz, 1H), 8.34 (t, J=5.6 Hz, 1H), 7.80-7.73 (m, 2H), 7.69-7.61 (m, 2H), 7.44 (d, J=5.0 Hz, 1H), 4.86-4.79 (m, 4H), 3.20 (t, J=6.2 Hz, 2H), 2.46-2.25 (m, 3H), 2.20 (d, J=7.9 Hz, 3H), 2.06-1.78 (m, 1H), 1.52-1.37 (m, 1H); MS (ESI(+)) m/e 438 (M+H)+.

Workup

  1. additionadded to the mixture via syringe slowly
  2. customThe mixture was quenched with water
  3. extractionthe separated aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b9a033fe316946b9bb84a2b6a268de50
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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